Ethyl Acetate → HCID 86607539, compound

Participants

Reaction Steps

Add sodium hypochlorite (150 mL) to a solution of (±)-[2-(3-hydroxymethyl-2,5-bis-methoxymethoxy-phenyl)-cyclopentyl]-(4-methoxymethoxy-phenyl)-methanone (1.69 g, 3.66 mmol) and tetrabutylammonium bromide (0.500 g, 1.55 mmol) in EtOAc. Stir the biphasic mixture vigorously for 2 hours at ambient temperature and separate the layers. Extract the aqueous solution with EtOAc (50 mL) and wash the combined organics with H2O (50 mL) and brine (25 mL), then dry (MgSO4), filter and concentrate to obtain the subtitled product (1.88 g, >95%) as an oil that may be used without purification. 1H NMR (CDCl3) δ 1.76-1.81 (m, 1H), 1.97-2.14 (m, 4H), 2.24-2.39 (m, 1H), 3.41 (s, 3H), 3.42 (s, 3H), 3.58 (s, 3H), 3.80-3.86 (m, 1H), 4.28-4.33 (m, 1H), 4.94-5.07 (m, 4H), 5,12 (s, 2H), 6.81 (d, J=8.9 Hz, 2H), 7.00 (d, J=3.1 Hz, 1H), 7.08 (d, J=3.1 Hz, 1H), 7.61 (d, J=8.9 Hz, 2H), 10.00 (s, 1H).

Provenance & Evidence