2-(3-Bromopropoxy)tetrahydro-2H-pyran → HCID 19907429, compound

Participants

Reaction Steps

To 17.5 ml of absolute n-hexane were added dropwise 530 mg of m-xylene and 1.40 g of potassium t-butoxide, followed by addition of 8.4 ml of 1.6M solution of n-butyl lithium in n-hexane over 5 minutes with stirring at a room temperature, and the mixture was refluxed for an hour to obtain a orange suspension. This reaction mixture was cooled with dry ice/acetone, and after adding at once a solution of 3.35 g 2-(3-bromopropyloxy)tetrahydropyran in absolute n-hexane with stirring, further stirred for 5 minutes, warmed to a room temperature and stirred at the same temperature overnight. To a pale yellow suspension thus obtained were added 20 ml of ice water and 50 ml of n-hexane. The separated organic layer was washed with water and a saturated sodium chloride aqueous solution, dried over magnesium sulfate, and evaporated under a reduced pressure to remove the solvent. The resulting oily residue was applied to a silica gel column and eluted with hexane/ethyl acetate (20:1) to obtain 913 mg of the title compound as a colorless liquid.

Provenance & Evidence