Dichloromethane → HCID 54438084, compound

HRID 582890Notes

Reaction equation

HRID 582890 reaction equation
[Cl:1][CH:2]([C:7](=[O:15])[CH2:8][CH2:9][CH2:10][CH2:11][CH2:12][CH2:13][CH3:14])[C:3]([O:5][CH3:6])=[O:4].P.C(Cl)Cl>[Ru].CO>[Cl:1][CH:2]([C@H:7]([OH:15])[CH2:8][CH2:9][CH2:10][CH2:11][CH2:12][CH2:13][CH3:14])[C:3]([O:5][CH3:6])=[O:4]

Participants

6

Reactant 3

HCID 6344DichloromethaneHCID 24404Phosphine2×HCID 54424532Methyl 2-chloro-3-oxodecanoate

Product 1

HCID 54438084HCID 54438084, compoundYield 95%

Reagents, catalysts & solvents 2

HCID 23950RutheniumCatalystHCID 887MethanolSolvent

Procedure

In a 500 ml Hastelloy-made autoclave having been purged with nitrogen were put 100 g (0.426 mol) of the methyl 2-chloro-3-oxodecanoate (VII) prepared in (1) above, 5 ml of a methylene chloride solution of 780 mg (0.426 mmol) of a ruthenium-optically active phosphine complex Ru2Cl4 [(+)-Tol-BINAP]2NEt3, and 300 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 yield 95.78 g (0.405 mol; yield: 95.0%) of the title compound.

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-3f3687ae078946c6bfd6495101d6f1fe
Source dataset
uspto-grants-1999_07
Patent number
US05925792

Reaction notes

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