Triethylamine → HCID 86691792, compound

Participants

Reaction Steps

43 g of 1-(3,5-bis(trifluoromethyl)benzyl)cyclopentanol and 16.7 g of triethylamine dissolved in 100 mL of methylene chloride was slowly charged into flask equipped with magnetic stirrer and 14.93 mL of methacryloyl chloride in 100 mL of dichloromethane cooled down to 0° C. The resultant mixture slowly warmed up to room temperature and allowed to stir at this temperature for 12 hours. Upon completion of the reaction as confirmed by thin layer chromatography, the mixture was quenched by pouring into 400 mL of deionized water and extracted further into methylene chloride. The methylene chloride extracts were then dried over sodium sulfate, filtered and concentrated in the rotary evaporator affording 34 g of 1-(3,5-bis(trifluoromethyl)benzyl)cyclopentyl methacrylate (˜65%) yield of as an amber oil. The oil was purified further by passing through a silica gel plug eluting with a 60/40 mixture of hexanes/methylene chloride affording 30 g of 1-(3,5-bis(trifluoromethyl)benzyl)cyclopentyl methacrylate (LG1) as pure product. 1H NMR (500 MHz, Acetone-d6): δ 7.97 (s, 1H), 7.76 (s, 2H), 5.99 (s, 1H, vinyl), 5.6 (s, 1H, vinyl), 3.56 (s, 2H), 2.23-1.70 (m, 8H), 1.80 (s, 3H).

Provenance & Evidence