Sodium Hydroxide → HCID 11845295, compound

Participants

Reaction Steps

Freshly prepared aq. NaOH (10 M in H2O, 5.02 mmol) was added to a stirring, room temperature solution of 5 (0.1949 g, 1.00 mmol) in MeOH (12.5 mL, 0.4 M) under N2. The reaction was then heated to reflux until the reaction was judged complete by TLC (0.5 h). The reaction was concentrated and then dissolved in 2 mL H2O. 10% aq. HCl was added dropwise until the pH=2. 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 0.1223 g (73.3%) of 6. 1H (CD3OD, 400 MHz): δ 3.18-3.07 (1H, m), 2.84-2.62 (3H, m), 2.08-1.96 (1H, m), 1.25 (3H, d, J=6.8 Hz) ppm. 13C (CD3OD, δ 164.49, 163.43, 131.67, 129.41, 40.87, 33.40, 23.61, 19.73 ppm. DEPT (CD3OD, 100 MHz): CH3 carbons: 19.73; CH2 carbons: 40.87, 23.61; CH carbons: 33.40 ppm. HPLC: 7.006 min.

Provenance & Evidence