Sodium Hydroxide → HCID 178480264, compound

Participants

Reaction Steps

To a solution of Example 3E (3.52 g, 17 mmol) in tetrahydrofuran (20 mL) was added sodium hydroxide (2.72 g, 68 mmol) in water (5.00 mL), followed by addition of a solution of 2-bromo-5-(trifluoromethyl)benzoyl chloride (3.85 g, 17 mmol) in tetrahydrofuran (5 mL) dropwise at 0° C. The mixture was stirred at room temperature for 1 hour then diluted with water (20 mL) and ethyl acetate (30 mL). The layers were separated and the organic extract was washed with brine, dried over magnesium sulfate, filtered, and concentrated. The residue was purified by column chromatography using an Analogix® Intelliflash280™ (SiO2, eluted with a gradient of 15-100% hexane in solvent B, solvent B: 10:1:0.5 ethyl acetate:methanol:triethylamine) to afford the title compound (6.3 g, 93%). 1H NMR (300 MHz, DMSO-D6) δ ppm 0.41-0.52 (m, 4H) 1.13-1.27 (m, 1H) 1.40 (s, 9H) 3.94 (s, 3H) 4.20 (d, J=6.74 Hz, 2H) 6.83 (s, 1H) 7.54 (dd, J=8.53, 2.18 Hz, 1H) 7.77-7.82 (m, 2H); MS (ESI) m/z 458 [M+H]+.

Provenance & Evidence