Triethyl phosphite → (4-Pentenyl)phosphonic acid diethyl ester

HRID 2354497Notes

Reaction equation

[P:1]([O:8][CH2:9][CH3:10])([O:5][CH2:6][CH3:7])[O:2]CC.I[CH2:12][CH2:13][CH2:14][CH:15]=[CH2:16]>>[CH2:9]([O:8][P:1]([CH2:16][CH2:15][CH2:14][CH:13]=[CH2:12])(=[O:2])[O:5][CH2:6][CH3:7])[CH3:10]

Participants

Reactant 2

HCID 31215Triethyl phosphite

HCID 109871725-Iodopent-1-ene

Product 1

HCID 13462469(4-Pentenyl)phosphonic acid diethyl ester

Conditions

Temperature: 130 °C

Procedure

1H NMR (CDCl3) δ=5.8 (m, 1H), 5.0 (m, 2H), 3.2 (t, 2H), 2.2 (sq, 2H), 1.8 (sq, 2H). Triethyl phosphite (400 mL, 2.3 mol, 3.5 eq.) was added to the 1-iodo-4-pentene, and the mixture was heated to 130° C. for three hours. Diethyl ethyl phosphonate was removed by fractional vacuum distillation, revealing the desired 4-pentenyl phosphonic acid diethyl ester which was used without further purification. 1H NMR (CDCl3) δ=5.7 (m, 1H), 4.8 (m, 2H), 4.0 (m, 4H), 2.0 (sq, 2H), 1.7 (m, 4H), 1.2 (t, 6H). 31P NMR (CDCl3) δ=33.3.

Workup

customDiethyl ethyl phosphonate was removed by fractional vacuum distillation
customwas used without further purification

Sources & evidence

ORD record: ord-d1086a9cd2ed4a0c806d8c29df662f8a
Source dataset: uspto-grants-2010_07
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US07754200B2

Reaction notes

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