Acetic Anhydride → HCID 14478577, compound

Participants

Reaction Conditions

Reaction Steps

A mixture of 1.23 g (5 mmol) of (S)-2-[3-hydroxy-3-methyl-4-pentynyl]-3,5,6-trimethyl-2,5-cyclohexadiene-1,4-dione ([α]D25 +11.3° CH2Cl2), 1.05 mL of triethylamine, 120 mg of 4-N,N-dimethylamino pyridine, and 0.6 mL of acetic anhydride in 8 mL of CH2CL2 was stirred at 25° C. under argon for 17 h. It was diluted with CH2CL2 (70 mL), washed with 1.0 N HCl, saturated NaHCO3 solution, water and dried over MgSO4. The crude material (1.6 g) was purified by flash chromatography on silica gol (50 g; 230-400 mesh). Elution with ether:petroleum ether (3:17) gave 1.47 g of (S)-2-[3-(acetyloxy)-3-methyl-4-pentynyl]-3,5,6-trimethyl-2,5-cyclohexadiene-1,4 -dione as a yellow oil, [α]D25 -21.42° (c, 0.994, CH2Cl2).

Provenance & Evidence