Phosphate → 2-(3-Bromopropoxy)tetrahydro-2H-pyran

Participants

Reaction Steps

A solution of 4.61 g. 3-bromopropanol in 150 ml. methylene chloride at 0° C. was treated with 5.1 ml. dihydropropyran followed by 55 mg. p-toluenesulphonic acid and then warmed to room temperature. After one hour, phosphate buffer (pH: 7.5) was added to the mixture. The organic layer was washed with brine, dried (Na2SO4) and evaporated. The yellow oil obtained was purified by chromatography on triethylamine-treated silica gel using a gradient solvent system (pure hexane--50% v/v ethyl ether/hexane) as eluent to give 2-(3-bromopropoxy)tetrahydro-2H-pyran in 69% yield as an oil, having a satisfactory NMR spectrum.

Provenance & Evidence