Acetyl chloride → HCID 54236183, compound

Participants

Reaction Conditions

Reaction Steps

To a suspension of AlCl3 (0.54 g, 4.05 mmol, 1.1 equiv) in CH2Cl2 (20 mL) is added acetyl chloride (0.28 mL, 4.05 mmol, 1.1 equiv). The resulting suspension is allowed to stir at -78° C. for 30 min, and a solution of 8-tert-butyl-2,3-dihydrobenzopyran (0.70 g, 3.68 mmol) in CH2Cl2 (5 mL) is added dropwise using an addition funnel. After the addition is complete, the reaction mixture (pale yellow precipitate) is allowed to warm to room temperature over 4 h. The resulting suspension is cooled to 0° C and quenched with water, washed with water and brine. The aqueous layers are extracted with CH2Cl2, the combined organic layer is dried (MgSO4), filtered and concentrated. The resulting off-white solid is recrystallized using hexanes to give the title compound (0.67 g, 79%) as white crystals.

Provenance & Evidence