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

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).

1. additionwas added slowly
2. stirringThe resulting mixture was stirred at −78° C. for 15 mins
3. customThe reaction was quenched by the addition of sat. NH4Cl aq (10 ml)
4. customThe organic layer was collected
5. extractionthe aqueous layer was extracted with EtOAc
6. dry with materialThe combined organic layers were dried over Na2SO4
7. concentrationconcentrated under reduced pressure
8. customPurification by flash chromatography (30 to 65% EtOAc-hexanes gradient)

ORD record

ord-c73722123e3c4e51b8d405778a874523

Source dataset

uspto-grants-2014_03

DOI

10.6084/m9.figshare.5104873.v1

Patent number

US08674137B2