Download e-book for iPad: Compendium of Organic Synthetic Methods Volume 5 by Michael B. Smith

By Michael B. Smith

ISBN-10: 0471867284

ISBN-13: 9780471867289

Offers man made chemists with a mode for quick retrieval of knowledge from the literature, directory fabric by way of response sort instead of by way of writer identify or book date. each one up to date quantity will current the newest man made tools for coaching of monofunctional and difunctional compounds. The association is logical and straightforward to persist with; sections are prepared in accordance with the prospective interconversions among the foremost sensible teams. allows man made chemists to maintain abreast of contemporary advancements and retrieve a selected piece of data fast and simply.

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Perkin I , 1492 (1981) 38 COMPENDIUM OF ORGANIC SYNTHETIC METHODS VOL 5 SECTION 38 Section 38 Alcohols from Esters 0 II C5H1 ,C-ONe NaBH4 polyethylene glycol , 0 11 CH3 ( CH2 ) 6-C -0Me 80% * C5H, CH20H JOC, NaBH4 t-BuOH, MeOH 46, 4584 (1981) CH3 (CH2) 6-CH20H Synth Comm, It C-NMe2 NaBH4 EtOH -SEt CH20H Synth Comm, LiBH4 +E-OEt (1982) 0 0 - NPle s 12, 463 79% ( Me0 ) B 11,599 93% (1981) 81% = JOC, 47, 1604 (1982) SECTION 38 ALCOHOLS FROM ESTERS COOEt 39 CH20H BH3*SMe2 89% THF, r e f l u x S y n t h e s i s , 439 (1981 1 JOC, 47, 3153 (1982) 94% JOC, 45, 1 (1980) 1 ) HSi(OEt)3 CsF H2C=CH (CH2)8-COOMe 2) $0 * H2C=CH ( CH2)8CH20H 70% S y n t h e s i s , 558 ( 1 9 8 1 ) 40 SECTION 3 8 COMPENDIUM OF ORGANIC SYNTHETIC METHODS VOL 5 34% Tetr Lett, EtCOOCH3 Cp2TiC1 t 21, 2171 and 2175 ( 1 9 8 0 ) OH I * Et-C-Pr 83% 1 H PrMgBr Tetr Lett, 21, 2171 a n d 2175 ( 1 9 8 0 ) 7 2% JOC, 45, 1828 (1980) 1 ) NaH, 1-BuX 0 II NsC-CH2-C-SBz 2 ) NaH, PhCH2X i-Bu -1 P4 z C - C - C H *OH I 3 ) NaBH4 CH2Ph Tetr Lett, 2, 3151 (1982) 76% ALCOHOLS AND PHENOLS FROM ETHERS AND E P O X I D E S S E C T I O N 39 R e l a t e d Methods: 41 C a r b o x y l i c A c i d s f r o m E s t e r s - S e c t i o n 23, P r o t e c t i o n of A l c o h o l s - S e c t i o n 45A H y d r o l y s i s o f E s t e r s i s c o v e r e d i n S e c t i o n 23 S e c t i o n 39 A l c o h o l s and P h e n o l s f r o m E t h e r s and E p o x i d e s BBr3, NaI 100% CH2C12, 15-crown-5 Me0 HO Tetr Lett, OMe 22, 4239 (1981 ) B B r 3 * SMe2 %80% R R Tetr Lett, 1, 3731 (1980) 0 OH OEt MeSiC13 Na I w Angew I n t Ed, 20, 690 (1981) 85% 42 COMPENDIUM OF ORGANIC SYNTHETIC METHODS VOL 5 S E C T I O N 39 OH OMe i 1 ) Me3Si I , p y r i d i n e 89% 2 ) CH30H Org Syn, 3,35 (1980) MeSSiMe3 R-OH o r PhSSiMe3 Tetr Lett, % , 21, 2305 90% (1980) S y n t h e s i s , 396 ( 1 9 8 1 ) SiC14 Ph-OMe Na I * Ph-OH S y n t h e s i s , 1048 ( 1 9 8 2 ) 90% S E C T I O N 39 ALCOHOLS AND PHENOLS FROM ETHERS AND E P O X I D E S 43 OH OMe 1 ) PhMeNNa, HMPT %80-90% R Syn t hes i s , 638 ( 1 980) L i A l H4 + benzene OMe OMe OH OEle 67% JCS Chem Comm, 507 (1980) OMe COOH COOlle JOC, 46, 1991 (1981) 44 COMPENDIUbl OF O R G A N I C SYNTHETIC METHODS VOL 5 SECTION 39 Additional examples of e t h e r c l e a v a g e s may be found i n S e c t i o n 45A ( P r o t e c t i o n o f Alcohols and P h e n o l s ) .

C . S . Perkin I , 1492 (1981) 38 COMPENDIUM OF ORGANIC SYNTHETIC METHODS VOL 5 SECTION 38 Section 38 Alcohols from Esters 0 II C5H1 ,C-ONe NaBH4 polyethylene glycol , 0 11 CH3 ( CH2 ) 6-C -0Me 80% * C5H, CH20H JOC, NaBH4 t-BuOH, MeOH 46, 4584 (1981) CH3 (CH2) 6-CH20H Synth Comm, It C-NMe2 NaBH4 EtOH -SEt CH20H Synth Comm, LiBH4 +E-OEt (1982) 0 0 - NPle s 12, 463 79% ( Me0 ) B 11,599 93% (1981) 81% = JOC, 47, 1604 (1982) SECTION 38 ALCOHOLS FROM ESTERS COOEt 39 CH20H BH3*SMe2 89% THF, r e f l u x S y n t h e s i s , 439 (1981 1 JOC, 47, 3153 (1982) 94% JOC, 45, 1 (1980) 1 ) HSi(OEt)3 CsF H2C=CH (CH2)8-COOMe 2) $0 * H2C=CH ( CH2)8CH20H 70% S y n t h e s i s , 558 ( 1 9 8 1 ) 40 SECTION 3 8 COMPENDIUM OF ORGANIC SYNTHETIC METHODS VOL 5 34% Tetr Lett, EtCOOCH3 Cp2TiC1 t 21, 2171 and 2175 ( 1 9 8 0 ) OH I * Et-C-Pr 83% 1 H PrMgBr Tetr Lett, 21, 2171 a n d 2175 ( 1 9 8 0 ) 7 2% JOC, 45, 1828 (1980) 1 ) NaH, 1-BuX 0 II NsC-CH2-C-SBz 2 ) NaH, PhCH2X i-Bu -1 P4 z C - C - C H *OH I 3 ) NaBH4 CH2Ph Tetr Lett, 2, 3151 (1982) 76% ALCOHOLS AND PHENOLS FROM ETHERS AND E P O X I D E S S E C T I O N 39 R e l a t e d Methods: 41 C a r b o x y l i c A c i d s f r o m E s t e r s - S e c t i o n 23, P r o t e c t i o n of A l c o h o l s - S e c t i o n 45A H y d r o l y s i s o f E s t e r s i s c o v e r e d i n S e c t i o n 23 S e c t i o n 39 A l c o h o l s and P h e n o l s f r o m E t h e r s and E p o x i d e s BBr3, NaI 100% CH2C12, 15-crown-5 Me0 HO Tetr Lett, OMe 22, 4239 (1981 ) B B r 3 * SMe2 %80% R R Tetr Lett, 1, 3731 (1980) 0 OH OEt MeSiC13 Na I w Angew I n t Ed, 20, 690 (1981) 85% 42 COMPENDIUM OF ORGANIC SYNTHETIC METHODS VOL 5 S E C T I O N 39 OH OMe i 1 ) Me3Si I , p y r i d i n e 89% 2 ) CH30H Org Syn, 3,35 (1980) MeSSiMe3 R-OH o r PhSSiMe3 Tetr Lett, % , 21, 2305 90% (1980) S y n t h e s i s , 396 ( 1 9 8 1 ) SiC14 Ph-OMe Na I * Ph-OH S y n t h e s i s , 1048 ( 1 9 8 2 ) 90% S E C T I O N 39 ALCOHOLS AND PHENOLS FROM ETHERS AND E P O X I D E S 43 OH OMe 1 ) PhMeNNa, HMPT %80-90% R Syn t hes i s , 638 ( 1 980) L i A l H4 + benzene OMe OMe OH OEle 67% JCS Chem Comm, 507 (1980) OMe COOH COOlle JOC, 46, 1991 (1981) 44 COMPENDIUbl OF O R G A N I C SYNTHETIC METHODS VOL 5 SECTION 39 Additional examples of e t h e r c l e a v a g e s may be found i n S e c t i o n 45A ( P r o t e c t i o n o f Alcohols and P h e n o l s ) .

Chem, 188 (1981) PROTECTION OF CARBOXYLIC ACIDS SECTION 30A 0 R-C-0-CH2 21 Na2S204 +R-COOH H 20/Me CN Synth Comm, 85-95% 12, 219 (1982) v Br-CH2 eMOOC@- 0 I1 R-C-ONa - n R-I-OCH, -(ot COOMe JCS Chem Comm, 1083 (1980) Angew Chem Int Ed, 2J, 780 (1982) rs R-C-OH CH2=CH-CH2SiMe3 0 + It R-C-OSiMe3 Tetr Lett, 1 ,835 (1980) nJ 90% COMPENDIUPI OF ORGANIC SYNTHETIC METHODS VOL 5 22 Me Si C 1 R-COOH R = C1 CH2CH2C1 - 0 II R-C-OSiMe3 SECTION 30A %70-90% alkyl , vinyl, ally1 , acetylenic, etc. Synthesis, 626 (1980) 0 (Me3Si)20 II R-C-OH H2S04 0 It e R-C-OSiMe3 '~70-90% Chem Lett, 1475 (1980) Ph 8 R-C-OH It 0 Chem Lett, 1551 (1981) SECTION 30A PROTECTION OF CARBOXYLIC ACIDS 23 The 5,6-dihydrophenanthridine protecting group may be activated and removed by oxidation: Ce+4, H20 cef4, C ~ O R'NH2 + + R-COOH 0 II R-C-NHR ' Chem Lett, 991 (1982) NaHS Used as a C-terminal protecting group in peptide synthesis.

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