Sodium Hydroxide → HCID 11299678, compound

Participants

Reaction Steps

Freshly prepared aq. NaOH (10 M in H2O, 4.84 mmol) was added to a stirring, room temperature solution of 38 (0.2689 g, 0.968 mmol) in MeOH (2.42 mL, 0.4 M) under N2. The reaction was heated to reflux until the reaction was judged complete by HPLC (30 min): The product was concentrated and then dissolved in 5 mL H2O. The product was extracted with EtOAc, then the aqueous layer was made acidic (pH=2) with the dropwise addition of 10% aq. HCl. The white solid that precipitated from the reaction was filtered off and washed with cold H2O. The solid was dried under vacuum overnight to obtain 39 as a pale pink solid (Note: An undesired impurity has a retention time of 10.956 min by HPLC. 1H (CD3OD, 400 MHz): δ 10.89 (1H, broad s), 7.22 (2H, d, J=8.3 Hz), 7.13 (2H, d, J=8.3 Hz), 6.69 (1H, s), 6.66 (1H, s), 2.82 (2H, t, J=7.1 Hz), 2.73 (2H, t, J=7.1 Hz) ppm. 13C (CD3OD, 100 MHz): δ 164.48, 142.15, 132.49, 131.15, 129.21, 125.97, 123.60, 122.88, 116.44, 37.92, 29.70 ppm. DEPT (CDCl3, 100 MHz): CH2 carbons: 37.92, 29.70; CH carbons: 131.15, 129.21, 122.88, 116.44 ppm. HPLC: 9.996 min.

Provenance & Evidence