Methanol → HCID 23047776, compound

HRID 2107139Notes

Reaction equation

HRID 2107139 reaction equation
[Br:1][CH:2]([CH2:6][CH2:7][CH2:8][CH2:9][CH2:10][C:11]1[CH:16]=[CH:15][C:14]([Cl:17])=[CH:13][CH:12]=1)[C:3]([OH:5])=[O:4].CO.[N+](=C)=[N-].[CH3:23][CH2:24]OCC>>[Br:1][CH:2]([CH2:6][CH2:7][CH2:8][CH2:9][CH2:10][C:11]1[CH:12]=[CH:13][C:14]([Cl:17])=[CH:15][CH:16]=1)[C:3]([O:5][CH2:23][CH3:24])=[O:4]

Participants

5

Reactant 4

HCID 887MethanolHCID 3283Diethyl Ether2×HCID 9550DiazomethaneHCID 23047782HCID 23047782, compound

Product 1

HCID 23047776HCID 23047776, compound

Procedure

To a solution of 31.0 g (0.097 mol) of 2-bromo-7-(4-chlorophenyl)heptanoic acid in 250 ml of absolute ether which contains 0.5 ml of methanol, a solution of about 0.16 mol of diazomethane in 300 ml of absolute ether is added drop by drop, with stirring, at room temperature, until the evolution of nitrogen ceases. Then the reaction mixture is concentrated by evaporation and the concentrate is chromatographed with toluene on silica gel. 18.1 g (56% of theory) is obtained of ethyl 2-bromo-7-(4-chlorophenyl)heptanoate, a colorless oil.

Workup

  1. concentrationThen the reaction mixture is concentrated by evaporation
  2. customthe concentrate is chromatographed with toluene on silica gel

Sources & evidence

ORD record
ord-65d1b4b7675c4404af804d530c438767
Source dataset
uspto-grants-1990_06
Patent number
US04933367

Reaction notes

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