Chloroform → Ethyl 3-oxobutyl(diethoxymethyl)phosphinate

HRID 5170

Reaction equation

C[Si]([PH:5]([CH:10]([O:14][CH2:15][CH3:16])[O:11][CH2:12][CH3:13])([O-:9])[O:6][CH2:7][CH3:8])(C)C.[CH:17]([C:19]([CH3:21])=[O:20])=[CH2:18].C(Cl)(Cl)Cl>O>[O:20]=[C:19]([CH3:21])[CH2:17][CH2:18][P:5]([CH:10]([O:14][CH2:15][CH3:16])[O:11][CH2:12][CH3:13])(=[O:9])[O:6][CH2:7][CH3:8]

Participants

Conditions

Temperature: 50 °C

Procedure

15.0 g of ethyl trimethylsilyl(diethoxymethyl)phosphonite are added dropwise to a stirred solution of 3.9 g of methyl vinyl ketone under an atmosphere of nitrogen at room temperature. The mixture is then heated to 50° C. for a period of 1 hour. The mixture is then allowed to cool to room temperature, 25 ml of chloroform is then added followed by 10 ml water and this mixture is vigorously stirred for a period of 0.5 h. The organic layer is then separated, dried over magnesium sulphate and concentrated under reduced pressure and the crude product distilled under reduced pressure to give ethyl 3-oxobutyl(diethoxymethyl)phosphinate, b.p. 130°-135° C./0.02 mbar, 31P=+45.3 ppm (CDCl3).

Workup

temperatureto cool to room temperature
customThe organic layer is then separated
dry with materialdried over magnesium sulphate
concentrationconcentrated under reduced pressure
distillationthe crude product distilled under reduced pressure

Sources & evidence

ORD record: ord-30eae213606d47d0a395349b420efeef
Source dataset: uspto-grants-1993_09
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US05243062

Linked notes

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