Acetyl chloride → HCID 21864953, compound

Participants

Reaction Conditions

Reaction Steps

A mixture of (3-amino-5,6,7,8-tetrahydronaphtho[2,3-b]furan-2-yl)(2,4-dichlorophenyl)methanone (150 mg, 0.46 mmol) from Example 142, acetyl chloride (0.16 mL, 2.3 mmol, 5.0 eq), and diisopropylethylamine polystyrene resin (245 mg, 0.92 mmol, 2.0 eq, 3.77 mol/g loading) in dichloroethane (4.6 mL) was shaken at 70° C. for 15 h. The resin was filtered and washed with dichloromethane (2×10 mL), methanol (2×10 mL), and dichloromethane (2×10 mL). The filtrate was evaporated in vacuo. Crystallization from ether-hexane gave 73.2 mg (35.8%) as a white solid. 1H-NMR (DMSO-d6) δ 7.82 (s, 1H), 7.62 (d, J=0.6 Hz, 1H), 7.61 (d, J=1.8 Hz, 1H), 7.46 (broad s, 2H), 2.84 (m, 4H), 2.20 (s, 6H), 1.73 (broad s, 4H); MS GC-MS (MH+=444/445); Rf=0.55 (25% ethyl acetate-hexane).

Provenance & Evidence