Methanol → (S)-alpha-(2-Chloroethyl)-5-isoxazolemethanol

Participants

Reaction Steps

Borane (18 ml, 1M in tetrahydrofuran) was added to a solution of (3aR)-tetrahydro-1-methyl-3,3-diphenyl-3H-pyrrolo[1,2-c][1,3,2]oxazaborole (1.3 ml, 1M in toluene) in tetrahydrofuran (10 ml) at −10° C. A solution of 3-chloro-1-(3-isoxazolyl)-1-propanone (Example 66(b)) (6 g, 37.6 mmol) in tetrahydrofuran (12 ml) was added slowly and then stirred at −10° C. to 20° C. for 18 h. Methanol was added and the solution was evaporated and the residue azeotroped with methanol. Purification by chromatography on silica eluting with petrol-ether gave the sub-title compound as a colourless oil (774 mg, 13%).

Provenance & Evidence