m-Chloroperbenzoic acid → Ethyl 2-diethoxyphosphinyloxiranecarboxylate

HRID 962399Notes

Reaction equation

HRID 962399 reaction equation
[CH2:1]([O:3][P:4]([O:13][CH2:14][CH3:15])([C:6](=[CH2:12])[C:7]([O:9][CH2:10][CH3:11])=[O:8])=[O:5])[CH3:2].C([O-])(O)=[O:17].[Na+].ClC1C=CC=C(C(OO)=O)C=1>C(Cl)Cl>[CH2:14]([O:13][P:4]([O:3][CH2:1][CH3:2])([C:6]1([C:7]([O:9][CH2:10][CH3:11])=[O:8])[CH2:12][O:17]1)=[O:5])[CH3:15]

Participants

5

Reactant 3

HCID 70297m-Chloroperbenzoic acidHCID 516892Sodium BicarbonateHCID 11085761Ethyl 2-(diethoxyphosphoryl)prop-2-enoate

Product 1

HCID 14973764Ethyl 2-diethoxyphosphinyloxiranecarboxylate

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

To a solution of 2.36 g (0.01 mole) of ethyl 2-diethoxyphosphinylpropenoate (J. Org. Chem., 43, 1259 (1978)) in 150 ml of methylene chloride is added 50 ml of 0.5 N aqueous NaHCO3 solution. The mixture is stirred rapidly at ambient temperature, while meta-chloroperbenzoic acid (0.01 mole) is slowly added. After stirring for about 6 hours longer, the methylene chloride layer is separated off and is washed with 0.5 N NaOH solution and then with water. It is dried with Na2SO4 and is evaporated to dryness to give ethyl 2-diethoxyphosphinyloxiranecarboxylate as an oil.

Workup

  1. additionis slowly added
  2. customthe methylene chloride layer is separated off
  3. washis washed with 0.5 N NaOH solution
  4. dry with materialIt is dried with Na2SO4
  5. customis evaporated to dryness

Sources & evidence

ORD record
ord-6208290f08754d989a6d990284c6d267
Source dataset
uspto-grants-1998_06
Patent number
US05760021

Reaction notes

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