Diethyl chlorophosphate → 1-Benzyl-2-diethylphosphonoimidazole

HRID 1181210Notes

Reaction equation

HRID 1181210 reaction equation
[CH2:1]([N:8]1[CH:12]=[CH:11][N:10]=[CH:9]1)[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.[Li+].CC([N-]C(C)C)C.[P:21](Cl)([O:26][CH2:27][CH3:28])([O:23][CH2:24][CH3:25])=[O:22]>C1COCC1>[CH2:1]([N:8]1[CH:12]=[CH:11][N:10]=[C:9]1[P:21]([O:26][CH2:27][CH3:28])([O:23][CH2:24][CH3:25])=[O:22])[C:2]1[CH:3]=[CH:4][CH:5]=[CH:6][CH:7]=1

Participants

5

Reactant 3

HCID 13139Diethyl chlorophosphateHCID 779181-BenzylimidazoleHCID 2724682Lithium diisopropylamide

Product 1

HCID 426371461-Benzyl-2-diethylphosphonoimidazole

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

A solution of 1-benzylimidazole (1.1 mmol) in THF was treated with LDA (1.1 mmol) at −78° C. for 1 h, and followed by addition of diethyl chlorophosphate (2 mmol), and stirred for 2 h. Extraction and chromatography gave 1-benzyl-2-diethylphosphonoimidazole as a yellow oil. TLC: Rf=0.35, 80% EtOAc-hexane.

Workup

  1. extractionExtraction and chromatography

Sources & evidence

ORD record
ord-257642a8c64c42ba97979f3cf0ecdc75
Source dataset
uspto-grants-2007_10
Patent number
US07285543B2

Reaction notes

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