HCID 118307095, compound → HCID 118307079, compound

Participants

Reaction Steps

To a mixture of (S)-4-methyl-2-(pent-4-en-2-yloxy)benzaldehyde (50 mg, 0.245 mmol) in diethyl ether (2 mL) was added methylmagnesium iodide (0.245 mL, 0.734 mmol) and the mixture was stirred at rt for 1 h. It was then diluted with water, extracted with EtOAc. The organic layer was dried over MgSO4, filtered and concentrated. The residue was purified by biotage, eluting with 25% EtOAc/hexane to obtain 1-(4-methyl-2-((S)-pent-4-en-2-yloxy)phenyl)ethanol (50 mg, 93%) as an oil. 1H NMR (400 MHz, CDCl3) δ 7.19 (dd, J=7.7, 3.8 Hz, 1H), 6.76 (d, J=7.8 Hz, 1H), 6.71 (s, 1H), 5.88 (ddtd, J=17.2, 10.3, 7.0, 3.5 Hz, 1H), 5.22-5.10 (m, 2H), 5.10-4.96 (m, 1H), 4.62-4.47 (m, 1H), 2.94 (dd, J=18.8, 5.4 Hz, 1H), 2.64-2.38 (m, 2H), 2.34 (s, 3H), 1.51 (d, J=6.6 Hz, 3H), 1.37 (dd, J=6.0, 4.0 Hz, 3H).

Provenance & Evidence