ethyl (S)-alpha-(t-butyldimethylsilyloxy)-alpha-phenylacetate → (S)-alpha-(t-Butyldimethylsilyloxy)-alpha-phenylacetaldehyde

HRID 1682749노트

반응식

HRID 1682749 반응식
[Si:1]([O:8][C@@H:9]([C:15]1[CH:20]=[CH:19][CH:18]=[CH:17][CH:16]=1)[C:10](OCC)=[O:11])([C:4]([CH3:7])([CH3:6])[CH3:5])([CH3:3])[CH3:2].[H-].C([Al+]CC(C)C)C(C)C>CCCCCC>[Si:1]([O:8][C@@H:9]([C:15]1[CH:16]=[CH:17][CH:18]=[CH:19][CH:20]=1)[CH:10]=[O:11])([C:4]([CH3:7])([CH3:6])[CH3:5])([CH3:3])[CH3:2]

참가 물질

4

반응물 2

HCID 10968419ethyl (S)-alpha-(t-butyldimethylsilyloxy)-alpha-phenylacetateHCID 21225700Diisobutylaluminumhydride

생성물 1

HCID 11075902(S)-alpha-(t-Butyldimethylsilyloxy)-alpha-phenylacetaldehyde

시약·촉매·용매 1

HCID 8058Hexane용매2회

실험 절차

Following a procedure similar to that described in Preparation 25, but using 8.8 g of ethyl (S)-α-(t-butyldimethylsilyloxy)-α-phenylacetate (prepared as described in Preparation 24), 300 ml of dry hexane and 30 ml of a 1M solution of diisobutylaluminum hydride in hexane, and then purifying the reaction product by column chromatography through silica gel, using a 1:60 by volume mixture of ethyl acetate and hexane as the eluent, the title compound was obtained having an Rf=0.29 (thin layer chromatography over silica gel, using a 1:80 by volume mixture of ethyl acetate and hexane as the developing solvent).

후처리

  1. customthat described in Preparation 25
  2. custompurifying the reaction product by column chromatography through silica gel
  3. additionby volume mixture of ethyl acetate and hexane as the eluent

출처 및 근거

ORD 기록
ord-30e3ad79da12441a994592394f5ec6b8
출처 데이터셋
uspto-grants-1997_06
특허 번호
US05635534

반응 노트

불러오는 중…