Nitromethane → 1-Cyclopropyl-2-nitroethan-1-ol

Temperature

0 °C

A mixture of THF (10 ml) and t-BuOH (10.00 ml) was cooled to 0° C. To this was added cyclopropanecarboxaldehyde (1.1 ml, 14.60 mmol) and nitromethane (1.18 ml, 21.88 mmol). After stirring 5 minutes 1M KOtBu (2.92 ml, 2.92 mmol) in THF was added slowly. During the addition a white solid formed. The mixture was allowed to warm as the bath warmed to rt overnight. The mixture was diluted with saturated aqueous NH4Cl and extracted with CH2Cl2 (3×). The combined organic layers were dried (MgSO4), filtered, and concentrated (no heat) to afford 1-cyclopropyl-2-nitroethanol (4-10, 1.9 g, 99%) as a clear oil which was sufficiently pure for use in the next step. 1H NMR (399 MHz, CDCl3): δ 4.56-4.52 (m, 2H); 3.72-3.64 (m, 1H); 2.42 (d, J=3.9 Hz, 1H); 0.99-0.90 (m, 1H); 0.68-0.59 (m, 2H); 0.52-0.44 (m, 1H); 0.39-0.32 (m, 1H).

1. additionwas added slowly
2. additionDuring the addition a white solid
3. customformed
4. temperatureto warm as the bath
5. temperaturewarmed to rt overnight
6. extractionextracted with CH2Cl2 (3×)
7. dry with materialThe combined organic layers were dried (MgSO4)
8. filtrationfiltered
9. concentrationconcentrated (
10. temperatureno heat)

ORD record

ord-3e3b4e29b57c4070a2746b73ca23a00a

Source dataset

uspto-grants-2016_03

DOI

10.6084/m9.figshare.5104873.v1

Patent number

US09278960B2