Methanol → (-)-Methyl (R)-3-hydroxyvalerate

HRID 610783ノート

反応式

HRID 610783 の反応式
[O:1]=[C:2]([CH2:8][CH3:9])[CH2:3][C:4]([O:6][CH3:7])=[O:5].CO.[H][H]>C(Cl)Cl.[Ru]>[OH:1][C@H:2]([CH2:8][CH3:9])[CH2:3][C:4]([O:6][CH3:7])=[O:5]

参加物

6

反応物 3

HCID 887MethanolHCID 121699Methyl 3-oxovalerateHCID 178418361HCID 178418361、化合物

生成物 1

HCID 11804797(-)-Methyl (R)-3-hydroxyvalerate収率 98.1%

試薬・触媒・溶媒 2

HCID 23950Ruthenium触媒HCID 6344Dichloromethane溶媒

実験手順

Into a 200-ml autoclave (made of Hastelloy) were introduced 50 g of methyl 3-oxopentanoate (manufactured by Wacker Chemicals Co., Ltd.) and 75 ml of methanol. The atmosphere in the autoclave was replaced with nitrogen gas. Thereto was added a solution prepared by dissolving 325 mg of Ru2Cl4 ((+)-(T)BINAP)2Et3N as a ruthenium-optically active phosphine complex in 3.8 ml of methylene chloride. Asymmetric hydrogenation was conducted at a reaction temperature of 30° C. and a hydrogen pressure of 30 atm. After the reaction mixture was thus reacted for 50 hours, it was taken out of the autoclave. The methanol was distilled off, and the residue was subjected to vacuum distillation to obtain 49.8 g of methyl (R)-3-hydroxypentanoate. Yield, 98%.

後処理

  1. additionThereto was added a solution
  2. customprepared
  3. customwas conducted at a reaction temperature of 30° C.
  4. customAfter the reaction mixture was thus reacted for 50 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-5dd474b8bae8449a987aa14641c66661
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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