Sodium Hydroxide → HCID 20638913, compound

Participants

Reaction Steps

To a 1 liter round bottom flask, charged with 11.58 g (30.0 mmol) of 13 in 100 mL of methanol was added 50 mL of 1N aqueous sodium hydroxide. The mixture was stirred for 2-3 h and then concentrated via rotary evaporation. The residue was transferred to a 250 mL round bottom flask in a total of 75 mL of de-ionized water. With vigorous stirring, the pH of the solution was adjusted to 1.5-2 by addition of 1N aqueous HCl, the product precipitating out as a white solid in the process. The mixture was vacuum filtered. The collected solids were rinsed with 3×50 mL aliquots of ice cold de-ionized water. The solids were air dried for 3 h and then under full vacuum pump pressure (<0.5 mm Hg) for 21 h to afford 10.07 g of the product (14) as a white solid (90%): 1H NMR (d6-DMSO) d 6.43 (1H, s), 6.35 (1H, s), 4.30 (1H, m), 4.12 (1H, m), 3.23 (2H, t), 3.10 (1H, m), 2.91 and 2.78 (3H, 2 s), 2.81 (1H, dd), 2.57 (1H, d), 2.30-2.13 (4H, m) and 1.79-1.10 (12H, m) ppm; 1H NMR (CD3OD) d 4.48 (1H, dd), 4.29 (1H, dd), 3.35 (2H, t), 3.19 (1H, m), 3.02 and 2.88 (3H, 2 s), 2.91 (1H, dd), 2.68 (1H, d), 2.43-2.23 (4H, m) and 1.83-1.21 (12H, m) ppm; Thin Layer Chromatography (Visualization with p-aminocinnimaldehyde spray); RP-18 Silica Gel, Rf=0.50 ({fraction (60/40)} methanol/water).

Provenance & Evidence