Ethyl Acetate → HCID 66828188, compound

Participants

Reaction Steps

To a solution of triethyl phosphonoacetate (0.601 mL, 3.00 mmol) in THF (10 mL) at 0° C. was added 1 M potassium tert-butoxide (3.00 mL, 3.00 mmol) in THF dropwise and the mixture was stirred for 30 mins at the same temperature. Then a solution of 2-(1-phenylcyclohexyl)acetaldehyde (405 mg, 2 0 mmol) in 4 ml of THF was added dropwise and the mixture was stirred for 0.5 hrs at 0° C. and for 1.5 hrs at room temperature. The mixture was added to EtOAc and washed with water (2×) and saturated NH4Cl. The resulting material was dried over Na2SO4 and evaporated to give an oily residue. It was purified by Combiflash (80 g silica gel) eluting with 5:95 EtOAc-hexane to give (E)-ethyl 4-(1-phenylcyclohexyl)but-2-enoate (213.7 mg). 1H NMR (400 MHz, CDCl3) δ ppm 7.27-7.37 (4 H, m), 7.15-7.23 (1 H, m), 6.60 (1 H, ddd, J=15.49, 7.91, 7.80 Hz), 5.66 (1 H, dt, J=15.60, 1.32 Hz), 4.12 (2 H, q, J=7.18 Hz), 2.39 (2 H, dd, J=7.80, 1.21 Hz), 2.11 (2 H, dd, J=13.07, 5.60 Hz), 1.33-1.66 (8 H, m), 1.24 (3 H, t, J=7.18 Hz).

Provenance & Evidence