3-Nitrophenol → HCID 59464179, compound

Participants

Reaction Steps

DEAD (1.97 mL, 10.8 mmol) was added dropwise to a stirred mixture of 3-nitrophenol (2.50 g, 18 mmol), (2S)-1-methoxypropan-2-ol (648 mg, 7.2 mmol) and triphenylphosphine (2.84 g, 10.8 mmol) in DCM (10 ml). The reaction mixture was stirred for 16 h then treated with saturated aqueous sodium hydrogen carbonate solution. The resultant mixture was partitioned and the organics were washed with 1M NaOH, dried and concentrated by evaporation. The residue was triturated with 1:1 EtOAC/hexanes. and filtered. The filtrate was concentrated by evaporation and the residue was purified by chromatography eluting with 25% EtOAc/hexane to give the title compound (1 g) as an oil; 1H NMR (400 MHz, DMSO) δ1.24 (d, 3H), 3.24 (s, 3H), 3.44-3.60 (m, 2H), 4.71-4.89 (m, 1H), 7.38-7.48 (m, 1H), 7.57 (t, 1H), 7.70-7.76 (m, 1H), 7.76-7.86 (m, 1H).

Provenance & Evidence