Triethyl phosphite → 2-((Diethoxyphosphoryl)methoxy)ethyl acetate

HRID 266233

Reaction equation

HRID 266233 reaction equation
[C:1]([O:4][CH2:5][CH2:6][O:7][CH2:8]Cl)(=[O:3])[CH3:2].[CH2:10]([O:12][P:13]([O:17]CC)[O:14][CH2:15][CH3:16])[CH3:11]>>[C:1]([O:4][CH2:5][CH2:6][O:7][CH2:8][P:13]([O:14][CH2:15][CH3:16])([O:12][CH2:10][CH3:11])=[O:17])(=[O:3])[CH3:2]

Participants

3

Reactant 2

HCID 31215Triethyl phosphiteHCID 10034810Acetic acid 2-chloromethoxy-ethyl ester

Product 1

HCID 139159842-((Diethoxyphosphoryl)methoxy)ethyl acetateYield 68.1%

Procedure

A mixture of 1-acetoxy-2-(chloromethoxy)ethane (67.8 g, 444 mmol) and triethylphosphite (81.3 g, 490 mmol) was heated at 105°-110° C. for 12 hours. Vigorous gas evolution was noted initially. The reaction mixture was next cooled to room temperature and the crude material purified by distillation (0.9 mmHg, 130°-134° C.) to afford 76.9 g (68%) of 1-acetoxy-2-(diethylphosphonomethoxy)ethane as a colorless liquid.

Workup

  1. temperaturewas heated at 105°-110° C. for 12 hours
  2. distillationthe crude material purified by distillation (0.9 mmHg, 130°-134° C.)

Sources & evidence

ORD record
ord-e9dc1b86fc4c471e93d694cab158d47d
Source dataset
uspto-grants-1997_07
Patent number
US05650510

Linked notes

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