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

HRID 590893Notes

Reaction equation

HRID 590893 reaction equation
Br[CH2:2][CH2:3][CH2:4][CH:5]=[CH2:6].[CH2:7]([O:9][P:10]([O:14]CC)[O:11][CH2:12][CH3:13])[CH3:8]>>[CH2:2]([P:10](=[O:14])([O:11][CH2:12][CH3:13])[O:9][CH2:7][CH3:8])[CH2:3][CH2:4][CH:5]=[CH2:6]

Participants

3

Reactant 2

HCID 31215Triethyl phosphiteHCID 707041-Pentene, 5-bromo-

Product 1

HCID 13462469(4-Pentenyl)phosphonic acid diethyl ester

Procedure

5-bromo-1-pentene was combined with triethylphosphite in the absence of solvent using microwave conditions at 150° C. to give diethyl 4-pentenylphosphonate. Diethyl 4-pentenylphosphonate was combined with bromotrimethyl silane and subsequently quenched with methanol to afford diethyl 4-pentenylphosphonic acid according to Scheme 8.

Workup

  1. customat 150° C.

Sources & evidence

ORD record
ord-698695d1b33f449b8bdad4e1c0e8db68
Source dataset
uspto-grants-2016_01
Patent number
US09234985B2

Reaction notes

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