Hydrochloric Acid → HCID 76594466, compound

Participants

Reaction Conditions

Reaction Steps

To a solution of 2-(2-(1-(3,5-bis(trifluoromethyl)benzyloxy)but-2-en-2-yl)phenyl)-1,3-dioxane (1.75 g, 3.8 mmol) in acetone (100 mL) and water (5 mL) at room temperature was added concentrated hydrochloric acid (0.4 mL). The resulting solution was stirred for 1.5 h. The reaction was quenched by the addition of saturated sodium bicarbonate, and poured into pentane. The organics were washed with water (2×), then brine, dried over magnesium sulfate, and concentrated. The crude residue was dissolved in ethanol (20 mL), cooled to 0° C., and treated with sodium borohydride (0.14 g, 3.8 mmol). After 5 min, the ice bath was removed and stirring continued for 30 min. The mixture was recooled to 0° C., and quenched by addition of saturated ammonium chloride. The mixture was extracted with ether, washed with water (2×), then brine, dried over magnesium sulfate, and concentrated. Column chromatography (5%-->25% EtOAc/Hex) gave 1.22 g (79%) as colorless oil and as a mixture of E- and Z-isomers. 1H-NMR (mixture, CDCl3, 300 MHz) δ 7.76 (s, 1H), 7.62 (s, 1.5H), 7.59 (s, 0.4H), 7.20-7.50 (m, 3.3H), 7.13 (d, J=7.0 Hz, 0.2H), 7.05 (m, 0.8H), 5.96 (q, J=6.7 Hz, 0.8H), 5.72 (q, J=7.0 Hz, 0.2H), 4.05-4.80 (m, 6.2H), 2.65 (m, 1H), 1.85 (d, J=7.0 Hz, 0.6H), 1.66 (bs, 0.4H), 1.47 (d, J=6.7 Hz, 2.4H).

Provenance & Evidence