Triethyl phosphite → Diethyl (2-phenylprop-2-en-1-yl)phosphonate

HRID 1531339Notes

Reaction equation

HRID 1531339 reaction equation
Br[CH2:2][C:3]([C:5]1[CH:10]=[CH:9][CH:8]=[CH:7][CH:6]=1)=[CH2:4].[CH2:11]([O:13][P:14]([O:18]CC)[O:15][CH2:16][CH3:17])[CH3:12]>>[CH2:11]([O:13][P:14]([CH2:2][C:3]([C:5]1[CH:10]=[CH:9][CH:8]=[CH:7][CH:6]=1)=[CH2:4])([O:15][CH2:16][CH3:17])=[O:18])[CH3:12]

Participants

3

Reactant 2

HCID 31215Triethyl phosphiteHCID 234998(3-bromoprop-1-en-2-yl)benzene

Product 1

HCID 21253621Diethyl (2-phenylprop-2-en-1-yl)phosphonate

Procedure

(Formula I, X=P(O), R1=phenyl, R=—OCH2CH3, n=2). α-(Bromomethyl)styrene was treated with an equimolar ratio of triethylphosphite at reflux for 1 h. After the mixture was cooled to room temperature, the by-product, ethyl bromide, was removed under reduced pressure, and the product α-(diethoxyphosphorylmethyl)styrene was obtained in quantitative yield as a yellowish syrup: 1H NMR (CDCl3) δ 1.20 (6H, t, 2×OCH2CH3, J 7.5 Hz), 3.05 (2H, d, CH2P(O), J 22.5 Hz), 4.00 (4H, m, 2×OCH2CH3), 5.35 (1H, d, olefinic proton, J 6.0 Hz), 5.50 (1K, d, olefinic proton, J 6 Hz), 7.25-7.55 (5H, m, aromatic protons).

Workup

  1. temperatureat reflux for 1 h
  2. customthe by-product, ethyl bromide, was removed under reduced pressure

Sources & evidence

ORD record
ord-8528d13f72714ea0a7c121c54844a83a
Source dataset
uspto-grants-2001_03
Patent number
US06197905B1

Reaction notes

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