Triethylamine → HCID 53950019, compound

Participants

Reaction Steps

To a stirred solution of tert-butyl 4-hydroxy-2-hydroxymethyl-6-tetrahydropyranyloxyhexanoate (0.28 g) and triethylamine (0.56 g) in methylene chloride (20 ml), mesylchloride (0.56 g) dissolved in methylene chloride (10 ml) was added dropwise under nitrogen atmosphere and ice-cooling. The mixture was stirred for 2 hours at room temperature and concentrated in vacuo. Saturated aqueous sodium bicarbonate solution was added to the oily residue and extracted with ethyl acetate. The organic layer was washed with saturated aqueous sodium bicarbonate solution, 1N hydrochloric acid, water and saturated aqueous sodium chloride solution. The organic layer was dried over anhydrous magnesium sulfate and concentrated in vacuo. The oily residue was dissolved in benzene (20 ml), and 1,8-diazabicyclo[5.4.0]undec-7-ene (0.2 g) was added to the solution. The mixture was stirred for 3 hours. Aqueous citric acid solution was added to the mixture and extracted with ethyl acetate. The organic layer was washed with saturated aqueous sodium bicarbonate solution, water and saturated sodium chloride solution. The organic layer was dried over anhydrous magnesium sulfate and concentrated in vacuo. The oily residue was purified by a silica gel column chromatography to give 0.22 g (31%) of tert-butyl 4-mesyloxy-2-methylene-6-tetrahydropyranyloxyhexanoate.

Provenance & Evidence