Sodium Hydroxide → HCID 11845472, compound

Participants

Reaction Steps

Freshly prepared aq. NaOH (10 M in H2O, 13.04 mmol) was added to a stirring, room temperature solution of 64 (0.8402 g, 2.608 mmol) in MeOH (6.5 mL, 0.4 M) under N2. The reaction was heated to reflux until the reaction was judged complete by HPLC (10 min): The product was concentrated and then dissolved in 10 mL H2O. The product was extracted with EtOAc until the organic layer no longer turned yellow, then the aqueous layer was made acidic (pH=2) with the dropwise addition of 10% aq. HCl. The product oiled out of solution, so EtOAc was added, and the organic layer was removed, dried with Na2SO4, filter, concentrated to obtain 65 (0.3934 g, 51.3%) as a white solid (Note: An undesired impurity has a retention time of 11.066 min by HPLC): 1H (CD3OD, 400 MHz): δ 7.51 (1H, d, J=7.8 Hz), 7.24-7.16 (2H, m), 7.05 (1H, ddd, J=8.2, 6.3, 2.9 Hz), 6.72 (1H, s), 6.71 (1H, s), 2.96 (2H, t, J=8.0 Hz), 2.73 (2H, t, J=7.8 Hz)) ppm. 13C (CD3OD, 100 MHz): δ 164.48, 142.42, 133.71, 131.80, 128.79, 128.53, 125.89, 125.20, 123.54, 122.61, 116.38, 38.99, 28.20 ppm. DEPT (CDCl3, 100 MHz): CH2 carbons: 38.99, 28.20; CH carbons: 133.71, 131.80, 128.79, 128.53, 122.61, 116.38 ppm. HPLC: 10.035 min.

Provenance & Evidence