Trimethyl phosphite → phosphoenol-3-chloropyruvate

HRID 913205Notes

Reaction equation

HRID 913205 reaction equation
[P:1]([O:6]C)([O:4]C)[O:2]C.[Cl:8][CH:9](Cl)[C:10](=[O:16])[C:11]([O:13]CC)=[O:12]>>[CH:9](/[Cl:8])=[C:10](/[O:16][P:1]([OH:6])([OH:4])=[O:2])\[C:11]([OH:13])=[O:12]

Participants

3

Reactant 2

HCID 8472Trimethyl phosphiteHCID 86133302HCID 86133302, compound

Product 1

HCID 6438513phosphoenol-3-chloropyruvateYield 58%

Procedure

To trimethyl phosphite (10 mmol) cooled at 0-10° C. was added dropwise ethyl dichloropyruvate (10 mmol). After addition, the ice-bath was removed and the reaction was allowed to proceed at 70° C. for one hour to give the ethyl/dimethyl ester of 3-chlorophosphoenolpyruvate. It was purified by flash chromatography (hexanes/ethyl acetate, 1:1, v/v) to give 1.5 g (58% yield) of 4:1 mixture of the Z- and E-isomers.

Workup

  1. additionAfter addition
  2. customthe ice-bath was removed

Sources & evidence

ORD record
ord-3d04185d08fd499eb5401ae992293baa
Source dataset
uspto-grants-2011_09
Patent number
US08026278B2

Reaction notes

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