Methyl bromoacetate → Methyl [ethoxy(4-phenylbutyl)phosphoryl]acetate
Reaction equation
Br[CH2:2][C:3]([O:5][CH3:6])=[O:4].[C:7]1([CH2:13][CH2:14][CH2:15][CH2:16][P:17]([O:21]CC)[O:18][CH2:19][CH3:20])[CH:12]=[CH:11][CH:10]=[CH:9][CH:8]=1>>[CH2:19]([O:18][P:17]([CH2:2][C:3]([O:5][CH3:6])=[O:4])([CH2:16][CH2:15][CH2:14][CH2:13][C:7]1[CH:8]=[CH:9][CH:10]=[CH:11][CH:12]=1)=[O:21])[CH3:20]Participants
3
Procedure
A mixture of 16.9 g. (0.11 mole) of methyl bromoacetate and 5.0 g. (0.019 mole) of (4-phenylbutyl)phosphonous acid, diethyl ester was heated on a 140°-150° oil bath until distillation of ethyl bromide was detected. An additional 16 g. (0.063 mole) of (4-phenylbutyl)phosphonous acid, diethyl ester was then gradually added to the reaction mixture. Heating was then continued for 45 minutes. After cooling to 100°, excess reagent was removed in vacuo to give 25 g. of crude product (Rf =0.25 silica gel/ethyl acetate). Impurities with higher Rf values were separated by flash chromatography using ethyl acetate. As a result, 18.3 g. of [ethoxy(4-phenylbutyl)phosphinyl]acetic acid, methyl ester were obtained.
Workup
- additionA mixture of 16.9 g