2-Nitropropane → HCID 67509137, compound

Participants

Reaction Conditions

Reaction Steps

1,1,3,3-Tetramethylguanidine (620 μL, 5 mmol) was added slowly to a cold, 0° C., stirring solution of benzyloxy acetaldehyde (4.6 g, 31 mmol) and 2-nitropropane (30 mL, 333 mmol) in 100 mL of anhydrous THF. The reaction was stirred at 0° C. for ten minutes then allowed to warm to room temperature and stirred for 18 hours. The reaction was concentrated under reduced pressure and the product purified by column chromatography (5 to 50% ethyl acetate in hexanes) to give the title compound as a clear liquid (6.4 g, 27 mmol, 84%). 1H NMR (CDCl3, 400 MHz) δ 1.58 (s, 3H), 1.63 (s, 2H), 2.87-2.89 (d, J=5.0 Hz, 1H), 3.48-3.53 (dd, 6.8, 9.8 Hz, 1H), 3.60-3.63 (dd, J=4.5, 9.8 Hz, 1H) 4.29-4.33 (m, 1H), 4.57 (s, 2H), 7.32-7.39 (m, 5H). LRMS (ESI/APCI) m/z 238 [M−H+].

Provenance & Evidence