Acetone Cyanohydrin → HCID 86630223, compound

Participants

Reaction Steps

To a solution of 2-(1-((3,5-bis(trifluoromethyl)benzyloxy)methyl)-1,3-dihydroisobenzofuran-1-yl)ethanol (250 mg, 0.60 mmol) and triphenylphosphine (390 mg, 1.5 mmol) in tetrahydrofuran (2.5 mL) at 0° C. was added acetone cyanohydrin (0.163 mL, 1.8 mmol), followed immediately by the addition of diethyl azodicarboxylate (0.234 mL, 1.5 mmol). The reaction was allowed to gradually warm to room temperature in the dewar overnight. The reaction was diluted with ether, washed with water, then saturated sodium bicarbonate, then water, then brine, dried over magnesium sulfate, and concentrated. Column chromatography (12%-->19% EtOAc/Hex) gave 214 mg (84%) as a colorless oil. 1H-NMR (CDCl3, 300 MHz) δ 7.77 (s, 1H), 7.66 (s, 2H), 7.35 (m, 2H), 7.25 (m, 1H), 7.18 (d, J=6.7 Hz, 1H), 5.14 (s, 2H), 4.64 (s, 2H), 3.65 (s, 2H), 2.38 (m, 2H), 2.22 (m, 1H), 2.07 (m, 1H); 13C-NMR (CDCl3, 126 MHz) δ 140.9, 140.0, 139.4, 131.8 (q, J=33.6 Hz), 128.9, 128.0, 127.2, 123.4 (q, J=273 Hz), 121.7, 121.6, 121.5, 119.7, 88.9, 76.2, 73.1, 72.1, 32.4, 11.8. Mass spec.: 430.09 (MH)+.

Provenance & Evidence