Pivalaldehyde → 1-(2-Nitrophenyl)-2,2-dimethyl-1-propanol

Participants

Reaction Conditions

Reaction Steps

Under a nitrogen atmosphere, a solution of 1-iodo-2-nitrobenzene (3.0 g, 12 mmol) in anhydrous THF (30 mL) was cooled to minus 40° C., and then phenylmagnesium chloride (2 M in THF, 7.2 mL, 14.5 mmol) was added dropwise at a rate that the temperature would not exceed minus 35° C. After the mixture was stirred for 20 minutes at minus 40° C., trimethylacetaldehyde (1.85 mL, 16.8 mmol) was added dropwise and the mixture was stirred for another 30 minutes at minus 40° C. The mixture was gradually warmed up to room temperature, quenched with saturated ammonium chloride (60 mL), poured into water (60 mL), and extracted with ethyl acetate three times (60 mL each). The combined organic phase was dried over Na2SO4, and concentrated in vacuo. The residue was purified by silica gel column chromatography to yield (RS)-1-(2-nitrophenyl)-2,2-dimethyl-1-propanol (1.82 g, 72%) as a yellow solid. 1H NMR (400 MHz, CDCl3): δ 7.82 (d, 1H, J=6.4 Hz, Ph-H), 7.76 (d, 1H, J=6.4 Hz, Ph-H), 7.61 (t, 1H, J=6.4 Hz, Ph-H), 7.39 (t, 1H, J=6.4 Hz, Ph-H), 5.39 (d, 1H, J=2.8 Hz, Ph-CH), 2.14 (d, 1H, J=3.2 Hz, OH), 0.89 (s, 9H, C(CH3)3).

Provenance & Evidence