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

HRID 1901208ノート

反応式

HRID 1901208 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-b0554e574ef84a8496b6b20024fc9b95
出典データセット
uspto-grants-1996_11
特許番号
US05576340

反応ノート

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