Triacetoxyperiodinane → HCID 118307095, compound

Participants

Reaction Steps

A mixture (S)-(4-methyl-2-(pent-4-en-2-yloxy)phenyl)methanol (260 mg, 1.260 mmol), Dess-Martin periodinane (642 mg, 1.513 mmol) in DCM (10 mL) was stirred at rt for 1 h. It was then diluted with EtOAc, washed with sat. NaHCO3 and water. The organic layer was dried over MgSO4, filtered and concentrated to obtain an oil, which was then purified by biotage, eluting with 10% EtOAc/hexane to isolate (S)-4-methyl-2-(pent-4-en-2-yloxy)benzaldehyde (90 mg, 35%) as an oil. 1H NMR (400 MHz, CDCl3) δ 10.44 (s, 1H), 7.75 (d, J=8.1 Hz, 1H), 6.87-6.78 (m, 2H), 5.88 (ddt, J=17.1, 10.1, 7.1 Hz, 1H), 5.21-5.10 (m, 2H), 4.59 (sxt, J=6.1 Hz, 1H), 2.63-2.51 (m, 1H), 2.51-2.42 (m, 1H), 2.40 (s, 3H), 1.40 (d, J=6.1 Hz, 3H).

Provenance & Evidence