Water → HCID 67350060, compound

Participants

Reaction Conditions

Reaction Steps

Methyl 3-chloro-3-oxopropanoate (9.4 ml, 87 mmol) was added into a solution of N-allyl-4-fluorobenzenamine (12 g, 79 mmol), DIEA (15 ml, 87 mmol) and DMAP (0.97 mg, 7.9 mmol) in CH2Cl2 (200 mL) at 0° C. under nitrogen. The reaction was stirred at 0° C. for 1 hour. The reaction mixture was poured into ice and water, extracted with CH2Cl2, washed with saturated aqueous NaHCO3 and brine. The organic layer was dried with Na2SO4, filtered and concentrated. The residue was purified by flash column chromatography (50% EtOAc in hexane) to afford the product (18.3 g, 92% yield) as brown oil. 1H NMR (400 MHz, CDCl3): δ 7.16-7.22 (m, 2H), 7.08-7.12 (m, 2H), 5.80-5.90 (m, 1H), 5.07-5.17 (m, 2H), 4.27-4.32 (m, 2H), 3.67 (s, 3H), 3.20 (s, 2H).

Provenance & Evidence