Dichloromethane → t-Butyl (triphenylphosphoranylidene)propionate

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The t-butyl (triphenylphosphoranylidene)propionate was prepared as follows: Triphenylphosphine (33 g), t-butyl 2-bromopropionate (22 g) and triethylamine (12.7 g) were dissolved in ethyl acetate (150 ml), and stirred and heated under reflux for 48 hr, under an atmosphere of nitrogen. Methylene chloride (300 ml) was added to the cooled solution; the mixture was thoroughly washed with sodium hydroxide solution (10% w/w, 300 ml), water (200 ml) and brine; and dried (MgSO4). The solvent was evaporated and the residual oil triturated with hexane (2×200 ml) to give t-butyl (triphenylphosphoranylidene)propionate (33 g, 67%) as a yellow powder; mp 144°-151°; partial NMR (250 MHz, CDCl3): 1.0(br signal, 9H, t-butyl), 1.55(d, J=14.4 Hz, 3H, CH3), 7.3-7.9(complex m, 15H, ArH).

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