CID 406 → HCID 178445043, compound

Participants

Reaction Steps

To a stirred suspension of dry sodium hydride (3.13 g, 124.07 mmol) in dry THF (100 ml) at room temperature was added dropwise a solution of dimethyl 2-oxopropyl)-phosphonate (20.61 g, 124.07 mmol) in dry THF (50 ml) under N2. The reaction mixture was stirred for 1 h, then cooled in an ice-bath and treated with a solution of n-butyllithium (7.95 g, 124.07 mmol) in hexane, causing a dark brown solution to be formed. Stirring was continued for 1 h at 0° C., followed by dropwise addition of 1-bromo2-butyne.1 (15 g, 112.79 mmol) in THF (30 ml). The reaction mixture was gradually warmed to room temperature and after 1 h (TLC monitoring) the reaction mixture was quenched with ice-water, HCl 1M to pH about 4 and extracted, twice, with ethyl acetate. The organic layer was washed with brine and chromatographed on silica gel using EtOAc as eluent. Rf=0.38 (silica gel, ethylacetate), yield 18 g (73%).

Provenance & Evidence