Phosphonic acid, P-(chloromethyl)-, diethyl ester → Diethoxyphosphinylmethylthioacetate

HRID 1646188Notes

Reaction equation

HRID 1646188 reaction equation
[C:1]([O-:4])(=[S:3])[CH3:2].C([N+](CCCC)(CCCC)CCCC)CCC.Cl[CH2:23][P:24](=[O:31])([O:28][CH2:29][CH3:30])[O:25][CH2:26][CH3:27]>O1CCCC1>[CH2:26]([O:25][P:24]([CH2:23][O:4][C:1](=[S:3])[CH3:2])([O:28][CH2:29][CH3:30])=[O:31])[CH3:27]

Participants

4

Reactant 2

HCID 76633Phosphonic acid, P-(chloromethyl)-, diethyl esterHCID 178477078HCID 178477078, compound

Product 1

HCID 53962055DiethoxyphosphinylmethylthioacetateYield 70.4%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

A solution of tetra-n-butylammonium thioacetate (12.8 g, 0.041 mol) and diethyl chloromethylphosphonate (5 g, 0.027 mol) is stirred in tetrahydrofuran (30 ml) overnight at room temperature. After evaporation of the solvent, the residue is purified by silica gel chromatography (2:1 heptane:acetone as eluant) to give diethoxyphosphinylmethylthioacetate (4.3 g). 1H-NMR: 4H, m, 4.20-4.11 ppm; 2H, d, 3.23; 3H, s, 2.40; 6H, m, 1.33.

Workup

  1. customAfter evaporation of the solvent
  2. customthe residue is purified by silica gel chromatography (2:1 heptane:acetone as eluant)

Sources & evidence

ORD record
ord-13e26aa07aa14c0cb045627c731bee0a
Source dataset
uspto-grants-1993_01
Patent number
US05179085

Reaction notes

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