Hydrochloric Acid → HCID 69516717, compound

Participants

Reaction Conditions

Reaction Steps

A mixture of 3-chloro-6-hydroxy-2-isopropyl-5-methylbenzaldehyde (1.83 g, 8.6 mmole), K2CO3 (2.38 g, 17.3 mmole) and ethyl 4,4,4-trifluorocrotonate (2.17 g, 12.9 mmole) in anhydrous DMF (10.0 mL) was heated to 90° C. under a dry N2 atmosphere for 18 hrs. The mixture was then cooled, poured into 0.5 N HCl (50 ml) and extracted with EtOAc (2×50 mL). The combined extracts were washed with brine (50 mL), dried over MgSO4, filtered and concentrated in vacuo to give a dark oil which was subject to flash chromatography (silica gel) and eluted with 50% CH2Cl2/hexanes to give a yellow oil (2.1 g, 68%): GCMS m/z 362.0 (M+). 1H NMR (CDCl3/400 MHz) 8.07 (s, 1H), 7.02 (s, 1H), 5.64 (q, 1H, J=7.0 Hz), 4.23 (m, 2H), 3.39 (s, 3H), 3.23 (m, 1H), 1.26 (m, 3H), 1.12 (m, 6H).

Provenance & Evidence