HCID 19815433, compound → HCID 15698115, compound

Participants

Reaction Steps

Ethyl 3-Carboethoxy-4-(4-methylphenyl)-4-(oxo)-butanal (10.00 g), trifluoroacetic anhydride (50 mL) and trifluoroacetic acid (2 drops) were mixed and stirred at 0° over ice and allowed to warm to room temperature. After 3 hours, more trifluoroacetic anhydride (50 mL) together with trifluoroacetic acid (2 drops) were added at room temperature. The next day, the solvent was removed in vacuo and the residue partitioned between 1N NaOH (200 mL) and ethyl acetate (200 mL). The layers were separated and the organic layer washed with 1N NaOH (2×200 mL). The organic layer was dried (MgSO4) and the solvent removed in vacuo to yield a brown oil (9.95 g) which was flash chromatographed in 99:1 hexane/ethyl acetate to yield 2.57 g of an off-white solid; m.p. 79.0°-80.5°. NMR (200 MHz, CDCl3) δ 7.88 (d, 2H, J=9Hz); 7.42 (d, 1H, J=2Hz); 7.26 (d, 2H, J=9Hz); 6.83 (d, 1H, J=2Hz); 4.34 (q, 2H, J=7Hz); 2.40 (s, 3H); 1.34 (t, 3H, J=7Hz). Anal. Calcd. for C14H14O3 : C, 73.03; H 6.13. Found: C, 73.52; H, 6.30.

Provenance & Evidence