Hydrochloric Acid → Benzyl 2(R)-benzyl-4-oxopentanoate

HRID 2380127ノート

反応式

HRID 2380127 の反応式
[CH2:1]([C@H:8]([CH2:19][CH:20]=[CH2:21])[C:9]([O:11][CH2:12][C:13]1[CH:18]=[CH:17][CH:16]=[CH:15][CH:14]=1)=[O:10])[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.Cl.CN(C)C=[O:26]>O.[Pd](Cl)Cl>[CH2:1]([C@H:8]([CH2:19][C:20](=[O:26])[CH3:21])[C:9]([O:11][CH2:12][C:13]1[CH:18]=[CH:17][CH:16]=[CH:15][CH:14]=1)=[O:10])[C:2]1[CH:3]=[CH:4][CH:5]=[CH:6][CH:7]=1

参加物

6

反応物 3

HCID 313Hydrochloric AcidHCID 6228DimethylformamideHCID 14989078Benzyl 2(S)-benzyl-4-pentenoate

生成物 1

HCID 14989079Benzyl 2(R)-benzyl-4-oxopentanoate収率 86%

試薬・触媒・溶媒 2

HCID 24290Palladium Chloride触媒HCID 962Water溶媒

実験手順

A suspension of 500 mg (5 mmoles) of cuprous chloride and 180 mg (1 mmole) of palladium chloride in a mixture of 5 ml of dimethylformamide and 0.6 ml of water was stirred for 1 hour under an atmosphere of oxygen. At the end of this time, 1.41 g(5.03 mmoles) of benzyl 2(S)-benzyl-4-pentenoate (prepared as described in Preparation 18) was added to the mixture. The mixture was then stirred for an additional 5 hours at room temperature and under an atmosphere of oxygen, after which the reaction mixture was poured into 100 ml of 1N aqueous hydrochloric acid, and the mixture was extracted with methylene chloride. The extract was dried over anhydrous magnesium sulfate, the solvent was removed by distillation under reduced pressure, and the residue was purified by medium pressure silica gel column chromatography (using a 5:1 by volume mixture of hexane and ethyl acetate as eluent), to give 1.28 g (yield 86%) of the title compound as a colorless oily substance.

後処理

  1. stirringThe mixture was then stirred for an additional 5 hours at room temperature and under an atmosphere of oxygen
  2. extractionthe mixture was extracted with methylene chloride
  3. dry with materialThe extract was dried over anhydrous magnesium sulfate
  4. customthe solvent was removed by distillation under reduced pressure
  5. customthe residue was purified by medium pressure silica gel column chromatography (
  6. additionby volume mixture of hexane and ethyl acetate as eluent),

出典と根拠

ORDレコード
ord-ee08565e8a1942848c16b2407b2924f4
出典データセット
uspto-grants-1994_11
特許番号
US05364844

反応ノート

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