Acetonitrile → 3-Hydroxy-3-(3-nitrophenyl)propanenitrile

Participants

Reaction Steps

To a solution of CH3CN (0.7 ml, 16 mmol) in THF (10 ml) was added LDA (8 ml, 2M in THF, 16 mmol) at −78° C. and the mixture was stirred at this temperature for 10 min. A chilled (−78° C.) solution of nitrobenzaldehye (10) (2.0 g, 13 mmol) in THF (15 ml) was added slowly. The resulting mixture was stirred at −78° C. for 15 mins. The reaction was quenched by the addition of sat. NH4Cl aq (10 ml) and the mixture allowed to warm to room temperature. The organic layer was collected and the aqueous layer was extracted with EtOAc. The combined organic layers were dried over Na2SO4 and concentrated under reduced pressure. Purification by flash chromatography (30 to 65% EtOAc-hexanes gradient) gave 3-hydroxy-3-(3-nitrophenyl)propanenitrile (11) as colorless oil, Yield (1.9 g, 77%); 1H NMR (400 MHz, CDCl3) δ 8.30 (t, J=3.2 Hz, 1H), 8.21-8.24 (m, 1H), 7.76-7.80 (m, 1H), 7.71 (t, J=8.0 Hz, 1H), 5.20 (t, J=2.4 Hz, 1H), 2.22 (d, J=6.0 Hz, 2H), 1.24 (s, 1H).

Provenance & Evidence