Triphenylphosphine → HCID 54494149, compound

Participants

Reaction Steps

A solution of triphenylphosphine (1.82 g) in tetrahydrofuran was added dropwise to a stirred solution of N-chlorosuccinimide (1.08 g) in tetrahydrofuran. After 10 minutes a solution of tert butyl 2-(2,3-dihydro-6-hydroxymethyl-4-oxo-5-phenyl-4H-1,3-oxazin-3-yl)-2-methylpropanoate (2.0 g) in tetrahydrofuran was added. The mixture was stirred overnight and partitioned between ether and water, and the organic phase washed (brine), dried (magnesium sulphate) and evaporated. The residue was purified by dry column chromatography on silica gel, eluting with dichloromethanelhexane (2:1) to give tert butyl 2-(6-chloromethyl-2,3-dihydro-4-oxo-5-phenyl-4H-1,3-oxazin-3-yl)-2-methylpropanoate (1.49 g) as a white solid, m.p. 128-129° C.

Provenance & Evidence