Isobutylene → HCID 86653600, compound

Participants

Reaction Steps

A solution of methyl (4RS,6RS)-6-(4-chloro-3-(trifluoromethyl)phenyl)-4-(hydroxymethyl)-6-methylcyclohex-1-enecarboxylate (Example 7, Step 9; 36.7 mg, 0.101 mmol) in dichloromethane (2 mL) was placed in a sealable tube, treated with p-toluenesulfonic acid hydrate (96 mg, 0.506 mmol) and cooled on dry ice. Liquid isobutylene (1-2 mL) was added, the tube was sealed and the mixture was stirred at rt for 72 h. After this time, the tube was cooled and unsealed, and the isobutylene was allowed to evaporate. The resulting mixture was diluted with dichloromethane, washed with saturated aqueous sodium bicarbonate, dried over sodium sulfate and concentrated under vacuum to yield a residue. The residue was purified by column chromatography on silica gel, eluting with 5-25% ethyl acetate-hexane, to provide methyl (4RS,6RS)-4-(tert-butoxymethyl)-6-(4-chloro-3-(trifluoro-methyl)phenyl)-6-methylcyclohex-1-enecarboxylate (22 mg, 52%). Mass spectrum m/z 436.0 (M+NH4+). 1H NMR (400 MHz, CDCl3) δ 7.55 (d, J=2.2 Hz, 1 H), 7.37 (d, J=8.6 Hz, 1 H), 7.30 (dd, J=8.4, 2.2 Hz, 1 H), 7.27 (dd, J=5.5, 2.9 Hz, 1 H), 3.64 (s, 3 H), 3.15 (dd, J=8.8, 4.4 Hz, 1 H), 3.07 (dd, J=8.6, 6.4 Hz, 1 H), 2.47 (m, 1 H), 1.96 (m, 1 H), 1.69 (m, 1 H), 1.64 (s, 3 H), 1.54 (m, 2 H), 1.11 (s, 9 H).

Provenance & Evidence