Hydrochloric Acid → HCID 178444524, compound

Participants

Reaction Steps

To 20.5 g of 2-butyl-7,8-difluorochroman-2-ol which was dissolved in 70 mL of DMF, 25.1 g bromo-trans-4-pentylcyclohexylmethane and 11.7 g of anhydrous potassium carbonate were added, and heated to reflux for 1 hour. After the reaction solution was poured into 10% hydrochloric acid, and stirred for a while, the solution was extracted with toluene. An organic layer was washed using 10% hydrochloric acid twice, water, a 5% sodium hydroxide aqueous solution twice, water, a saturated sodium hydrogen carbonate aqueous solution twive, and a saturated saline solution in that order, and dried using anhydrous magnesium sulfate. The solvent was evaporated under a reduced pressure, and the obtained brown oily material was purified by carrying out column chromatography (silica gel, hexane), recrystallization (acetone/methanol), distillation under a reduced pressure (227° C./0.6 mmHg), column chromatography (silica gel, hexane/toluene), recrystallization (acetone/methanol), and recrystallization (acetone/methanol), to obtain 8.8 g of 2-butyl-7,8-difluoro-6-(trans-4-pentylcyclohexylmethoxy)chroman (Ie) as colorless crystals.

Provenance & Evidence