Sulfuric Acid → HCID 12383845, compound

Participants

Reaction Conditions

Reaction Steps

A solution of ethyl 2-(fur-2-oyl)acetate (5.38 g, 29.5 mmol) and potassium hydroxide (2.70 mL, 2.7 g, 48.1 mmol) in water (70 mL) was stirred overnight at rt. sodium nitrite (2.038 g, 29.5 mmol) in water (10 mL) was added and cooled down to 0° C. A solution of 6N sulfuric acid in water (14 mL) was added drop wise and stirred for 15 min (precipitate was formed). Ether was added and the water layer was extracted twice with ether. The combined organic layers were washed with water, dried and evaporated. Crystallization with CH2Cl2 gave (E)-2-(furan-2-yl)-2-oxoacetaldehyde oxime 54 (2.52 g, 61.3%). NMR (400 MHz, CDCl3) 6.59 (q, J=3.5 and 1.5 Hz, 1H), 7.55 (dd, J=3.5 and 0.8 Hz, 1H), 7.72 (m, 1H), 7.96 (s, 1H), 8.27 (br s, 1H).

Provenance & Evidence