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Extra info for Compendium of Organic Synthetic Methods Volume 5
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) $0 * H2C=CH ( CH2)8CH20H 70% S y n t h e s i s , 558 ( 1 9 8 1 ) 40 SECTION 3 8 COMPENDIUM OF ORGANIC SYNTHETIC METHODS VOL 5 34% Tetr Lett, EtCOOCH3 Cp2TiC1 t 21, 2171 and 2175 ( 1 9 8 0 ) OH I * Et-C-Pr 83% 1 H PrMgBr Tetr Lett, 21, 2171 a n d 2175 ( 1 9 8 0 ) 7 2% JOC, 45, 1828 (1980) 1 ) NaH, 1-BuX 0 II NsC-CH2-C-SBz 2 ) NaH, PhCH2X i-Bu -1 P4 z C - C - C H *OH I 3 ) NaBH4 CH2Ph Tetr Lett, 2, 3151 (1982) 76% ALCOHOLS AND PHENOLS FROM ETHERS AND E P O X I D E S S E C T I O N 39 R e l a t e d Methods: 41 C a r b o x y l i c A c i d s f r o m E s t e r s - S e c t i o n 23, P r o t e c t i o n of A l c o h o l s - S e c t i o n 45A H y d r o l y s i s o f E s t e r s i s c o v e r e d i n S e c t i o n 23 S e c t i o n 39 A l c o h o l s and P h e n o l s f r o m E t h e r s and E p o x i d e s BBr3, NaI 100% CH2C12, 15-crown-5 Me0 HO Tetr Lett, OMe 22, 4239 (1981 ) B B r 3 * SMe2 %80% R R Tetr Lett, 1, 3731 (1980) 0 OH OEt MeSiC13 Na I w Angew I n t Ed, 20, 690 (1981) 85% 42 COMPENDIUM OF ORGANIC SYNTHETIC METHODS VOL 5 S E C T I O N 39 OH OMe i 1 ) Me3Si I , p y r i d i n e 89% 2 ) CH30H Org Syn, 3,35 (1980) MeSSiMe3 R-OH o r PhSSiMe3 Tetr Lett, % , 21, 2305 90% (1980) S y n t h e s i s , 396 ( 1 9 8 1 ) SiC14 Ph-OMe Na I * Ph-OH S y n t h e s i s , 1048 ( 1 9 8 2 ) 90% S E C T I O N 39 ALCOHOLS AND PHENOLS FROM ETHERS AND E P O X I D E S 43 OH OMe 1 ) PhMeNNa, HMPT %80-90% R Syn t hes i s , 638 ( 1 980) L i A l H4 + benzene OMe OMe OH OEle 67% JCS Chem Comm, 507 (1980) OMe COOH COOlle JOC, 46, 1991 (1981) 44 COMPENDIUbl OF O R G A N I C SYNTHETIC METHODS VOL 5 SECTION 39 Additional examples of e t h e r c l e a v a g e s may be found i n S e c t i o n 45A ( P r o t e c t i o n o f Alcohols and P h e n o l s ) .
H$Bu )' L i 8 * R-C-OCH2SCH3 subst. Ph, -CH20Ph Tetr Lett, FI R-C-OBZ 10% Pd/C 3,4539 29-72% (1982) R-COOH >go% Synthesis, 929 (1980) H / K [Co(CN) ] removes benzyl ester protecting groups from amino asids and pe3tides in 83-94% yields. Z. 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.
B. Nucleophilic additions to aldehydes, forming alcohols. C. Coupling of aldehydes to give diols. Section 34A: Reductions o f Aldehydes to Alcohols wCHo Na2S204 H20/dioxane/DMF JOC, + - CH20H 63% 45, 4126 (1980) 26 COMPENDIUM OF O R G A N I C SYLTHETIC METHODS VOL 5 L i A l H(OCEt3)3 S E C T I O N 34A CH20H WCH0 *- 100% JOC, C HO 46, 4628 (1981) Et20 Tetr Lett, 21 , 693 and 697 (1980) p o l y (2-v in y l p y r i d i n e ) -BH3 b THF -CH20H 87% JOC, C8H1 7-CH0 1 ) Et$%,, 2 ) H202, O' H CH ci -2 45, 2724 (1980) C8H17CH20H Tetr Lett, a,3963 75% (1980) SECTION 34A CgH1 gCHO 27 REDUCTIONS OF ALDEHYDES TO ALCOHOLS (TFA) 2BH*THF - CgH19CH20H JOC, 46, 96% 355 (1981) CH20H NaBH4 21 100% ErCl Reduces c o n j u g a t e d a l d e h y d e s i n t h e p r e s e n c e o f n o n - c o n j u g a t e d ones.
Compendium of Organic Synthetic Methods Volume 5 by Michael B. Smith