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

HRID 1682749ノート

反応式

HRID 1682749 の反応式
[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]

参加物

4

反応物 2

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

生成物 1

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

試薬・触媒・溶媒 1

HCID 8058Hexane溶媒2 回

実験手順

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).

後処理

  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

出典と根拠

ORDレコード
ord-30e3ad79da12441a994592394f5ec6b8
出典データセット
uspto-grants-1997_06
特許番号
US05635534

反応ノート

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