Sodium Hydroxide → HCID 178490931, compound

Participants

Reaction Steps

A mixture of Example 8E (3.54 g, 5.78 mmol) and 1.0 M aqueous sodium hydroxide (14.46 mL, 14.46 mmol) in ethanol (50 mL) was refluxed for 2 hours, cooled, and partitioned between water and ethyl acetate. The organic layer was washed with brine, dried with sodium sulfate, filtered and concentrated. The residue was purified on silica gel eluting with methanol (2% to 4%) in dichloromethane to give the title compound as a solid (2.13 g, 67%). 1H NMR (500 MHz, DMSO-d6) δ ppm 0.16-0.27 (m, 1H) 0.65-0.82 (m, 2H) 0.85-1.00 (m, 1H) 2.15-2.25 (m, 1H) 3.20 (s, 3H) 3.66-3.69 (m, 3H) 4.54 (s, 2H) 4.69-4.91 (m, 2H) 6.77-6.82 (m, 2H) 7.03 (s, 1H) 7.10-7.16 (m, 2H) 7.37-7.45 (m, 2H) 7.80 (s, 1H) 7.83-7.91 (m, 2H) 11.32 (s, 1H); MS (ESI+) m/z 550.1 (M+H)+.

Provenance & Evidence