Tetrahydrofuran → HCID 12727115, compound

Participants

Reaction Steps

Diethyl 2-oxopentyl-phosphonate (1.85 g, 8.26 mol) was added dropwise to a suspension of sodium hydride (0.50 g, 12.4 mmol, 60%) in dry THF (15 ml) followed by 3-acetyl pyridine (1.00 g, 8.26 mmol) at room temperature. The reaction mixture was stirred for 2 h at room temperature, quenched with acetic acid and was adjusted to pH-6. The reaction mixture was diluted with water and extracted with CHCl3. The combined organic layer was washed with brine, dried over anhydrous sodium sulfate, filtered and evaporated to dryness to yield the crude compound. Purification by column chromatography by means of neutral alumina using 10-15% ethyl acetate in petroleum ether as eluent afforded 600 mg (40%) of (E)-ethyl 3-(pyridin-3-yl)but-2-enoate as colorless liquid.

Provenance & Evidence