Dichloromethane → HCID 53719841, compound

HRID 582898Notes

Reaction equation

HRID 582898 reaction equation
[Cl:1][CH:2]([C:7](=[O:23])[CH2:8][CH2:9][CH2:10][CH2:11][CH2:12][CH2:13][CH2:14][CH2:15][CH2:16][CH2:17][CH2:18][CH2:19][CH2:20][CH2:21][CH3:22])[C:3]([O:5][CH3:6])=[O:4].ClC(C(=O)CC)C(OC)=O.C(Cl)Cl.P>[Ru].CO>[Cl:1][CH:2]([C@H:7]([OH:23])[CH2:8][CH2:9][CH2:10][CH2:11][CH2:12][CH2:13][CH2:14][CH2:15][CH2:16][CH2:17][CH2:18][CH2:19][CH2:20][CH2:21][CH3:22])[C:3]([O:5][CH3:6])=[O:4]

Participants

7

Reactant 4

HCID 6344DichloromethaneHCID 24404PhosphineHCID 545096Methyl 2-chloro-3-oxopentanoateHCID 13725780Methyl 2-chloro-3-oxooctadecanoate

Product 1

HCID 53719841HCID 53719841, compoundYield 95.3%

Reagents, catalysts & solvents 2

HCID 23950RutheniumCatalystHCID 887MethanolSolvent

Procedure

In a 500 ml Hastelloy-made autoclave having been purged with nitrogen were put 100 g (0.2886 mol) of the methyl 2-chloro-3-oxooctadecanoate (VII) prepared in (1) above, 2 ml of a methylene chloride solution of 260 mg (0.144 mol) 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 give 95.8 g (0.275 mol; yield: 95.3%) of the title compound (VIII) (melting point: 39-40° C.).

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-2ff2ae9ef42d425ca695e8c78948b109
Source dataset
uspto-grants-1999_07
Patent number
US05925792

Reaction notes

Loading…