Thionyl Chloride → HCID 21962640, compound

Participants

Reaction Steps

To a solution containing 5-[(3,5,5,8,8-pentamethyl-5,6,7,8-tetrahydro-2-naphthalenyl)methyl]-2-furoic acid, 7, (20.15 g, 61.77 mmol) in methylene chloride (310 mL), thionyl chloride (45 mL, 617 mmol) was added. The reaction was heated under reflux for 5 hours and another batch of thionyl chloride (45 mL, 617 mmol) was added. The reaction was stirred overnight at room temperature. The solution was concentrated to a syrup and filtered through a pad of silica gel (50 g), eluted with 3% ethyl acetate in hexanes, and concentrated in vacuo to afford 5-[(3,5,5,8,8-pentamethyl-5,6,7,8-tetrahydro-2-naphthalenyl)methyl]-2-furoyl chloride, 8 (17 g, 80% yield).

Provenance & Evidence