Methanol → Methyl 3-hydroxyoctanoate, (S)-

HRID 610785ノート

反応式

HRID 610785 の反応式
[O:1]=[C:2]([CH2:8][CH2:9][CH2:10][CH2:11][CH3:12])[CH2:3][C:4]([O:6][CH3:7])=[O:5].CO.[H][H]>C(Cl)Cl.[Ru]>[OH:1][C@@H:2]([CH2:8][CH2:9][CH2:10][CH2:11][CH3:12])[CH2:3][C:4]([O:6][CH3:7])=[O:5]

参加物

6

反応物 3

HCID 887MethanolHCID 89668Methyl 3-oxooctanoateHCID 178418361HCID 178418361、化合物

生成物 1

HCID 12550002Methyl 3-hydroxyoctanoate, (S)-収率 95.9%

試薬・触媒・溶媒 2

HCID 23950Ruthenium触媒HCID 6344Dichloromethane溶媒

実験手順

Into a 100-ml autoclave (made of Hastelloy) were introduced 20 g of methyl 3-oxooctanoate (manufactured by Inoue Perfumery Mfg. Co., Ltd.) and 50 ml of methanol. The atmosphere in the autoclave was replaced with nitrogen gas. Thereto was added a solution prepared by dissolving 140 mg of Ru2Cl4 ((-)-(T)BINAP)2Et3N as a ruthenium-optically active phosphine complex in 1.0 ml of methylene chloride. Asymmetric hydrogenation was conducted at a reaction temperature of 65° C. and a hydrogen pressure of 30 atm. After the reaction mixture was thus reacted for 6 hours, it was taken out of the autoclave. The methanol was distilled off, and the residue was subjected to vacuum distillation to obtain 19.4 g of methyl (S)-3-hydroxyoctanoate. Yield, 96%.

後処理

  1. additionThereto was added a solution
  2. customprepared
  3. customwas conducted at a reaction temperature of 65° C.
  4. customAfter the reaction mixture was thus reacted for 6 hours
  5. distillationThe methanol was distilled off
  6. distillationthe residue was subjected to vacuum distillation

出典と根拠

ORDレコード
ord-4b92dff144d248a589ce7194ce76eebe
出典データセット
uspto-grants-1999_12
特許番号
US05998668

反応ノート

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