Acetyl chloride → HCID 21202087, compound

Participants

Reaction Steps

To a stirred solution of 6-hydroxy-1-methyl-1-trifluoromethylisochroman (79 g, 0.34 mol) and triethylamine (120 mL, 0.88 mol) in THF (680 mL) was added acetyl chloride (31 mL, 0.44 mol) at 0° C., and the mixture was stirred at room temperature for 1 hr. The reaction was quenched by adding aqueous 1 N-HCl (400 mL), and extracted with ethyl acetate (500 mL). The extracts were washed with aqueous saturated NaHCO3 (100 mL) and brine (100 mL), dried over MgSO4, and concentrated in vacuo. The residue was purified by flash chromatography (Silica-gel, 15×20 cm, 6% ethyl acetate/hexane) to afford 6-acetoxy-1-methyl-1-trifluoromethylisochroman (83 g, 89%) as a colorless oil. 1H-NMR(CDCl3): 7.36 (d, J=7.2 Hz, 1H), 6.98 (dd, J=7.2, 2.5 Hz, 1H), 6.91 (d, J=2.5 Hz, 1H), 4.18-4.08 (m, 1H), 3.92 (dt, J=11, 5.4 Hz, 1H), 2.86 (t, J=5.4 Hz, 2H), 2.30 (s, 1H), 1.66 (s, 3H).

Provenance & Evidence