Nitroethane → HCID 419520, compound

Participants

Reaction Steps

To a solution of LiAlH4 (2M in THF) (1.4 mL, 2.8 mmol) in dry THF (110 mL) at 0° C., was slowly added 1-nitroethane (2.00 mL, 28 mmol) under argon. After 20 min at 0° C., nicotinaldehyde (2.64 mL, 28 mmol) was added in one portion. The mixture was stirred for 16 hours, while allowing the temperature to rise from 0° C. to room temperature. The reaction mixture was quenched by addition of 5 mL of 1M HCl, followed by addition of CH2Cl2 and Na2SO4. The resulting suspension was stirred for 15 minutes and then filtered. The filtrate was concentrated. The residue was then purified by column chromatography (40 g of SiO2) using EtOAc in hexane from 0% to 100% in order to give the product as an oil (3.2 g, 63%) as a mixture of diastereoisomers. LC-MS: [M+H] 183.4; Rt 0.41 min; (LCMS method 1). A) 1H NMR (400 MHz, CHCl3-d): 8.58-8.48 (m, 2H), 7.68 (d, 1H) 7.33-7.23 (m, 1H) 5.42-5.38 (m, 1H), 4.70-4.60 (m, 1H), 3.30-2.90 (brs, 1H), 1.46 (d, B) 1H NMR (400 MHz, CHCl3-d): 8.58-8.48 (m, 2H), 7.68 (d, 1H) 7.33-7.23 (m, 1H) 5.04 (d, 1H), 4.76-4.69 (m, 1H), 3.30-2.90 (brs, 1H), 1.31 (d, 3H).

Provenance & Evidence