Chlorotrimethylsilane → (E)-3-[Ethoxy(4-phenylbutyl)phosphinyl]-2-propenoic acid, methyl ester

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Reaction Conditions

Reaction Steps

A solution of (4-phenylbutyl)-phosphinic acid, ethyl ester (8.0 g, 35.4 mmols) in chloroform (40 ml) were added trimethylsilyl chloride (13.5 ml, 106 mmols) and triethylamine (19.7 ml, 142 mmols). The resulting mixture was stirred at 25° C. for 2.5 hours, after which it was concentrated in vacuo. To the residue were added methyl α-chloro=acrylate (20 g, 0.16 mole, prepared as described by C. S. Marvel and J. C. Cowan, J. Amer. Chem. Soc. 61, 3156 (1939)) and triethylamine (9.0 ml, 64 mmol). The resulting yellow mixture was stirred overnight at 65° C., resulting in an orange semisolid. The mixture was diluted with ethyl acetate and washed sequentially with 1N hydrochloric acid and saturated sodium bicarbonate solution, dried (MgSO4), and concentrated to an orange oil. The oil was chromotographed on LPS-1 silica gel, eluting with a gradient from 1:1 hexane:ethyl acetate to ethyl acetate, to give the title compound.

Provenance & Evidence