Hydrochloric Acid → 604787-90-8

Participants

Reaction Conditions

Reaction Steps

A solution of 8.36 g of 1-bromomethyl-4-(2,2-dibromovinyl)cyclohexane (trans/cis=about 3/1) in 20 mL of tetrahydrofuran was cooled to −78° C. under a nitrogen atmosphere. To the solution was added dropwise 24.3 mL of a 2.1 M methyl lithium diethyl ether solution over 30 minutes, followed by stirring for 2 hours while maintaining a temperature of −78° C. The reaction mixture was cooled in an ice bath, and 30 mL of a 1 N aqueous hydrochloric acid solution was added thereto. The reaction mixture was extracted with 30 mL of t-butyl methyl ether three times. The combined organic layer was washed sequentially with 100 mL of a saturated aqueous sodium hydrogen carbonate solution and 100 mL of a saturated aqueous sodium chloride solution, dried over sodium sulfate, filtered, and then concentrated under reduced pressure. The residue was subjected to silica gel column chromatography to give 4.68 g of 1-bromomethyl-4-ethynylcyclohexane represented by the following formula:

Provenance & Evidence