Tetrahydrofuran → 2-Diethylphosphonothiophene

HRID 1181206Notes

Reaction equation

HRID 1181206 reaction equation
[S:1]1[CH:5]=[CH:4][CH:3]=[C:2]1[Li].C1COCC1.[P:12](Cl)([O:17][CH2:18][CH3:19])([O:14][CH2:15][CH3:16])=[O:13]>>[CH2:15]([O:14][P:12]([C:2]1[S:1][CH:5]=[CH:4][CH:3]=1)([O:17][CH2:18][CH3:19])=[O:13])[CH3:16]

Participants

4

Reactant 3

HCID 8028TetrahydrofuranHCID 13139Diethyl chlorophosphateHCID 178418439HCID 178418439, compound

Product 1

HCID 42543912-Diethylphosphonothiophene

Procedure

A solution of 2-thienyllithium in THF (1 mmol) was added to a solution of diethyl chlorophosphate (1 mmol) at −78° C. under nitrogen. After 2 h the reaction was warmed to room temperature and quenched with brine. Extraction and chromatography afforded 2-diethylphosphonothiophene as a yellow oil. TLC: Rf=0.37, 50% EtOAc-hexane.

Workup

  1. customquenched with brine
  2. extractionExtraction and chromatography

Sources & evidence

ORD record
ord-2879aac836184e34a38735b19935bd90
Source dataset
uspto-grants-2007_10
Patent number
US07285543B2

Reaction notes

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