Tetrahydrofuran → HCID 57691462, compound

Participants

Reaction Steps

To a solution of 2-(3,5-bis(trifluoromethyl)benzyloxy)-N-methoxy-N-methylacetamide (5.0 g, 14 mmol) in tetrahydrofuran (20 mL, 247 mmol) at −78° C. was added (2-(1,3-dioxan-2-yl)phenyl)magnesium bromide (0.25M in tetrahydrofuran) (64 mL). The ice bath was replaced with a 0° C. bath and stirring continued for 1 h. The reaction was quenched by addition of saturated ammonium chloride. The mixture was diluted with pentane and the layers separated. The organics were washed with water, then brine, dried over magnesium sulfate, and concentrated. Flash chromatography (12% EtOAc/Hex) gave 3.20 g (49%) as a white crystalline solid. 1H-NMR (CDCl3, 300 MHz) δ 7.80 (s, 2H), 7.78 (s, 1H), 7.70 (d, J=7.6 Hz, 1H), 7.44 (m, 1H), 7.33 (m, 2H), 5.87 (s, 1H), 4.70 (s, 2H), 4.61 (s, 2H), 4.16 (dd, J=11.3, 4.9 Hz, 2H), 3.92 (m, 2H), 2.11 (m, 1H), 1.38 (d, J=13.7 Hz, 1H); 13C-NMR (CDCl3, 126 MHz) δ 202.2, 140.7, 136.9, 136.1, 131.7 (q, J=33.6 Hz), 130.9, 128.4, 127.7, 126.7, 123.4 (q, J=273 Hz), 121.7, 98.7, 75.2, 71.6, 67.4, 25.7.

Provenance & Evidence