Malonic Acid → HCID 86737519, compound

Participants

Reaction Steps

Titanium tetrachloride (2.5 ml., 25 mmol) in carbon tetrachloride (7.5 ml) was added to THF (60 ml) at 0° C. Malonic acid (1.0 g., 10 mmol) and trans 1,4-dichlorobut-3-en-2-one (1.4 g., 10 mmol) in THF (10 ml) was added. Pyridine (3.3 ml., 40 mmol) in THF (10 ml) was added dropwise over fifteen minutes at 0° C. The reaction mixture was stirred at room temperature for three hours, diluted with water (50 ml) and extracted with ether (50 ml., 2×25 ml). The extracts were washed with brine, N sodium bicarbonate solution, brine, dried (Na2SO4) and evaporated to give the title product (0.35 g., 12%). δ (CDCl3) 5.00 (2H, s, CH2), 6.91 (1H, d, J 5 Hz, CH=), 8.01 (1H, d, J 5 Hz, CH=), 9.68 (2H, s, --OH). νmax (CHCl3) 1720 cm-1.

Provenance & Evidence