Methyl bromoacetate → Methyl [ethoxy(4-phenylbutyl)phosphoryl]acetate

HRID 544098Notes

Reaction equation

HRID 544098 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

Reactant 2

HCID 60984Methyl bromoacetateHCID 13274712HCID 13274712, compound2×

Product 1

HCID 13603866Methyl [ethoxy(4-phenylbutyl)phosphoryl]acetate

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

  1. additionA mixture of 16.9 g
  2. distillationuntil distillation of ethyl bromide
  3. temperatureHeating
  4. temperatureAfter cooling to 100°
  5. customexcess reagent was removed in vacuo
  6. customto give 25 g
  7. customImpurities with higher Rf values were separated by flash chromatography

Sources & evidence

ORD record
ord-779baacbaf6449ccab6813ab4690c39f
Source dataset
uspto-grants-1984_05
Patent number
US04448772

Reaction notes

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