Acetic Acid → HCID 18410348, compound

Participants

Reaction Steps

A mixture of 67.1 mg (0.232 mmol) of compound 11, dry benzene (2 mL), 175 mL (0.927 mmol) of 1,8-diazabicyclo[5.4.0]undec-7-ene, and 40 mL (0.70 mmol) of acetic acid was refluxed for 1.5 hours. The reaction mixture was allowed to cool to room temperature, diluted with chloroform (10 mL), quenched with 1N HCl (1 mL) and separated. The organic layer was dried over MgSO4 and evaporated to yield the crude product. Purification by column chromatography (10 g of SiO2, 4.7% methanol-chloroform) gave 43.1 mg (0.138 mmol, 59.4% yield) of compound 5 as an oil. 1H NMR (CDCl3+5% CD3OD) δ 7.56 (1H, s), 6.80 (1H, s), 6.21 (1H, s), 5.14 (2H, s), 2.11 (3H, s); MS (ES, negative) 311.0 and 313.1; UV (KMOPS, pH 7.2) λmax (ε) 370 nm (15,000 M−1cm−1).

Provenance & Evidence