Triphenylphosphine → HCID 135474625, compound

Participants

Reaction Steps

A mixture of (2,5-dihydroxyphenyl)(4-hydroxyphenyl)methanone (1.0 g, 4.3 mmol), hydroxylamine hydrochloride (2.0 g, 29 mmol), pyridine (5 mL) and EtOH (30 mL) was heated to reflux. After stirring for 4 h, the reaction was cooled, poured into 2N HCl and extracted with EtOAc. The organic layer was dried over MgSO4, and concentrated to give a yellow foam (0.92 g, 87% yield). The product, (2,5-dihydroxyphenyl)(4-hydroxyphenyl)methanone oxime (0.9 g, 3.7 mmol) was taken in THF (25 mL) and triphenylphosphine (1.5 g, 5.6 mmol) first was added, followed by the dropwise addition of diethylazodicarboxylate (0.9 mL, 5.6 mmol). After 30 min the reaction was filtered, concentrated and the resulting oil was purified by column chromatography (eluent 30% EtOAc/hexanes) to give a solid. The solid was triturated with CH2Cl2, and filtered to give a solid (0.04 g, m.p. 266-268° C.); 1H NMR (DMSO-d6) 10.32 (s, 1H), 10.30 (s, 1H), 8.00 (d, 2H, J=8.7 Hz), 7.50 (d, 1H, J=8.7 Hz), 7.02 (d, 1H, J=2.3 Hz), 6.95 (d, 2H, J=8.7 Hz), 6.93 (dd, 1H, J=8.7 Hz, 2.4 Hz); MS m/e 228 (M+H)+.

Provenance & Evidence