Dichloromethane → HCID 54420244, compound

HRID 582894Notes

Reaction equation

HRID 582894 reaction equation
[Cl:1][CH:2]([C:7](=[O:10])[CH2:8][CH3:9])[C:3]([O:5][CH3:6])=[O:4].C(Cl)Cl.P>[Ru].CO>[Cl:1][CH:2]([C@H:7]([OH:10])[CH2:8][CH3:9])[C:3]([O:5][CH3:6])=[O:4]

Participants

6

Reactant 3

HCID 6344DichloromethaneHCID 24404PhosphineHCID 545096Methyl 2-chloro-3-oxopentanoate2×

Product 1

HCID 54420244HCID 54420244, compoundYield 95%

Reagents, catalysts & solvents 2

HCID 23950RutheniumCatalystHCID 887MethanolSolvent

Procedure

In a 100 ml Hastelloy-made autoclave having been purged with nitrogen were put 10 g (0.0607 mol) of the methyl 2-chloro-3-oxopentanoate prepared in (1) above, 0.2 ml of a methylene chloride solution of 26 mg (0.144 mmol) of a ruthenium-optically active phosphine complex Ru2Cl4 [(+)-Tol-BINAP]2NEt3, and 30 ml of methanol, and the mixture was allowed to react at 50° C. under a hydrogen pressure of 30 atm for 18 hours. Methanol was removed by evaporation to give 9.61 g (0.0577 mol; yield: 95.0%) of the title compound. Optical rotation [α]D25 =+6.35° (c=0.976, CHCl3)

Workup

  1. customhaving been purged with nitrogen
  2. customto react at 50° C. under a hydrogen pressure of 30 atm for 18 hours
  3. customMethanol was removed by evaporation

Sources & evidence

ORD record
ord-94d2d713ca3844f79770e2e5e8a8d759
Source dataset
uspto-grants-1999_07
Patent number
US05925792

Reaction notes

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