Sodium Hydroxide → HCID 11845293, compound

Participants

Reaction Steps

Freshly prepared aq. NaOH (10 M in H2O, 15.1 mmol) was added to a stirring, room temperature solution of 2 (0.6289 g, 3.02 mmol) in MeOH (7.6 mL, 0.4 M) under N2. The reaction was then heated to reflux until the reaction was judged complete by TLC (2.5 h). The reaction was concentrated, redissolved in EtOAc and H2O, and extracted with EtOAc. 10% aq. HCl was added dropwise until the pH=4, then the organic was removed, and the aqueous layer was extracted with EtOAc again. The combined organics were dried with Na2SO4, filtered, and concentrated. A small amount of CH2Cl2 and hexanes were added to the colored solid product, and the colored impurity was pipetted off. The remaining solid was dried to obtain 0.2371 g (43.6%) of 3 as an off-white solid. Note: The precipitation method used below appears to be the preferred protocol. 1H (CD3OD, 400 MHz): δ 2.75 (2H, t, J=6.8 Hz), 2.29 (2H, t, J=6.8 Hz), 1.29 (6H, s) ppm. 13C (CD3OD, 100 MHz): δ 166.15, 162.23, 130.46, 126.93, 47.10, 38.22, 26.62, 21.52 ppm. DEPT (CD3OD, 100 MHz): CH3 carbons: 26.62; CH2 carbons: 47.10, 21.52 ppm: LCMS: 181.4 (M+1); 163.6 ((M+1)−18). HPLC: 7.538 min.

Provenance & Evidence