Methyl Acrylate → HCID 86681335, compound

Participants

Reaction Steps

In a 250 mL round-bottomed flask was dissolved tert-butyl (1S,2S)-1-(3-bromopyrazin-2-yl)-2-(2,3-difluorophenyl)hex-5-enylcarbamate (354.6 mg, 0.757 mmol) in methylene chloride (16 mL) to give a colorless solution. Methyl acrylate (0.21 mL, 2.3 mmol) and Grubbs-If catalyst (32.1 mg, 0.038 mmol) were added, and the mixture was stirred under reflux for 3 h under nitrogen. TLC showed complete conversion. Volatile components were removed in vacuo and the residue was purified by flash column chromatography upto 50% ethyl acetate/hexane to afford the desired product (335 mg, 84%) as a colorless oil: 1H NMR (400 MHz, CHLOROFORM-d) δ ppm 8.31 (s, 1H) 8.28 (s, 1H) 6.98-7.14 (m, 3H) 6.80-6.94 (m, 1H) 5.76 (d, J=16.56 Hz, 1H) 5.59-5.71 (m, 1H) 5.42 (d, 0.1-9.54 Hz, 1H) 3.71 (s, 3H) 3.59-3.69 (m, 1H) 2.09-2.29 (m, 2H) 1.96-2.04 (m, 1H) 1.83-1.95 (m, 1H) 1.37 (s, 9H).

Provenance & Evidence