Hydrochloric Acid → (E)-4-(2,2-difluorovinyl)-4'-(prop-1-en-1-yl)-1,1'-bi(cyclohexane)

Participants

Reaction Steps

Difluorodibromomethane (29.9 g) was dissolved in THF (100 ml), and then a tris(diethylamino)phosphine (63.4 g) THF (20 ml) solution and an (E)-4′-(prop-1-en-1-yl)-[1,1′-bi(cyclohexane)]-4-carbaldehyde (20.0 g) THF (20 ml) solution were sequentially added dropwise in an ice bath under a nitrogen atmosphere. After completion of the reaction, 1 N hydrochloric acid was added, and extraction was carried out with toluene. An organic layer was washed with a saturated aqueous solution of sodium chloride, a saturated aqueous solution of sodium hydrogencarbonate and water, and then the resultant solution was dried over anhydrous magnesium sulfate and concentrated under reduced pressure, and thus a colorless oily matter was obtained. The resultant material was subjected to silica gel column chromatography (heptane) and recrystallization using Solmix A-11 (registered trademark) (Japan Alcohol Trading Co., Ltd.), and thus compound (1-B) was obtained as a white needle crystal (7.7 g).

Provenance & Evidence