2-prop-2-ynoxyacetyl chloride

Conditions: temp:0.00; pressure:0.00; stir:; See reaction.notes.procedure_details.

Procedure: Prop-2-ynyloxyacetyl chloride (1.74 g) in tetrahydrofuran (20 ml) was added dropwise over 5 min. to a stirred solution of dimethylamine (12 ml of 33% solution in ethanol) in tetrahydrofuran (15 ml) at ambient temperature. After 30 minutes the solvent was evaporated and the residue was partitioned between saturated aqueous sodium bicarbonate (20 ml) and ethyl acetate (30 ml). The aqueous layer was separated and then re-extracted with ethyl acetate (20 ml). The combined ethyl acetate extracts were washed with brine (20 ml), dried over sodium sulphate and then evaporated. There was thus obtained the title compound as a liquid (1.15 g). NMR Spectrum: (CDCl3) 2.47 (t, 1H), 2.96 (s, 3H), 3.02 (s, 3H), 4.27 (s, 2H), 4.33 (d, 2M); Mass Spectrum: M+H+ 142. After 30 minutes the solvent was evaporated the residue was partitioned between saturated aqueous sodium bicarbonate (20 ml) and ethyl acetate (30 ml) The aqueous layer was separated re-extracted with ethyl acetate (20 ml) The combined ethyl acetate extracts were washed with brine (20 ml) dried over sodium sulphate evaporated