Sodium Hydroxide → HCID 102041455, compound

Participants

Reaction Steps

A mixture of mesylate (3) (1.435 g, 4.5 mmol) and anhydrous aluminium trichloride (720 mg, 5.4 mmol) in distilled 1,2-dichloroethane (12 mL) was stirred was stirred under argon at reflux temperature for 10 min then cooled to r.t. The reaction mixture was diluted with water (24 mL) and THF (24 mL), made basic with 5 M NaOH (30 mL) and stirred at r.t. 30 min before extraction with DCM (2×50 mL), then with AcOEt (2×50 mL). The combined organic layers were dried with MgSO4 and concentrated under reduced pressure to afford a pale yellow oil. Purification by flash chromatography (AcOEt/cyclohexane 0/10 to 3/7, v/v) afforded the desired enone (4) as colorless oil (920 mg, 92%).

Provenance & Evidence