Water → HCID 67484700, compound

Participants

Reaction Conditions

Reaction Steps

2-Methyl-4-hydroxy-6-methoxycarbonylbenzofuran (Method 12; 412 mg, assumed 1.0 mmol) was stirred in anhydrous DMF (10 ml) and the solution treated sequentially with potassium carbonate (690 mg, 5 mmol, 5 eq) and 1-iodo-2-methylpropane (442 mg, 276 μl, 2.4 mmol, 2.4 eq). The reaction mixture was stirred at 90° C. for 3 hours, then cooled and poured into water; the resulting mixture was extracted twice with ethyl acetate, the extracts dried (MgSO4) and evaporated in vacuo to yield a brown oil. This was chromatographed (50 g Bondelut, eluting with hexane containing ethyl acetate, 0-100%) to give the title compound as a clear oil contaminated with ca 15% of the corresponding iso-butyl ester. NMR: 1.02 (d, 6H), 2.06 (sept, 1H), 2.45 (s, 3H), 3.84 (s, 3H), 3.91 (d, 2H), 6.66 (s, 1H), 7.24 (s, 1H), 7.66 (s, 1H); the spectrum also contained signals consistent with isobutyl ester, ca 15 mol %.

Provenance & Evidence