Triethyl phosphite → Triethyl 2-phosphonopropionate

HRID 1464193Notes

Reaction equation

HRID 1464193 reaction equation
Br[CH:2]([CH3:8])[C:3]([O:5][CH2:6][CH3:7])=[O:4].[P:9]([O:16]CC)([O:13][CH2:14][CH3:15])[O:10][CH2:11][CH3:12]>>[CH2:11]([O:10][P:9]([CH:2]([CH3:8])[C:3]([O:5][CH2:6][CH3:7])=[O:4])([O:13][CH2:14][CH3:15])=[O:16])[CH3:12]

Participants

3

Reactant 2

HCID 31215Triethyl phosphiteHCID 79040Ethyl 2-bromopropionate

Product 1

HCID 107155Triethyl 2-phosphonopropionateYield 74.3%

Procedure

A mixture of 5.1 mL (39 mmol) of ethyl 2-bromopropionate and 14 mL (79 mmol) of triethyl phosphite was heated to 130°-140° C. and 2.2 mL of bromoethane (bp 38°-45 ° C.) was collected by distillation. Then unreacted triethyl phosphite was removed by distillation (23°-85° C. at 6-0.2 torr), leaving 6.9 g (74% yield) of the above ester as a colorless liquid: 1H NMR (CDCl3)δ 0.84-1.05 (m, 12H), 2.61 (d of q, 1H, J=23, 7 Hz), 3.60-3.85 (m, 6H).

Workup

  1. temperaturewas heated to 130°-140° C.
  2. distillation2.2 mL of bromoethane (bp 38°-45 ° C.) was collected by distillation
  3. customThen unreacted triethyl phosphite was removed by distillation (23°-85° C. at 6-0.2 torr)

Sources & evidence

ORD record
ord-632090002ba24389b0f5c6216f2157f0
Source dataset
uspto-grants-1994_04
Patent number
US05302752

Reaction notes

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