Nitromethane → 2-(2-Nitro-vinyl)-thiophene

Participants

Reaction Steps

Sodium acetate (3.6 g, 43.90 mmol) and methylamine hydrochloride (3.01 g, 44.57 mmol) were added to a stirred solution of thiophene-2-carbaldehyde (5 g, 44.64 mmol) in methanol (95.64 mL). This was followed by dropwise addition of nitro methane (108.08 g, 1770.14 mmol) over a period of 5 minutes. The resulting mixture was stirred at room temperature for 2 hours. The reaction was monitored by TLC (10% ethylacetate in hexane). The reaction mixture was partitioned between water and DCM. The organic layer was washed with water, brine solution, dried over Na2SO4 and concentrated. Purification by column chromatography on silica gel (5% ethylacetate in hexane) afforded 1 g of the product (15% yield).

Provenance & Evidence