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With water; potassium carbonate; In tetrahydrofuran; at 20℃; for 3h;
Add a saturated solution of potassium carbonated (3.5 mL) to a solution of acetic acid 2,3-dihydrobenzofuran-6-yl ester (0.250, 1.403 mmol) in tetrahydrofuran (7.0 mL) and stir at room temperature for 3 h. Dilute with ethyl acetate (100 mL) and wash with water (2 x 100 mL), saturated aqueous sodium chloride (100 mL), dry (sodium sulfate), filte, concentrate and purify (HPLC, eluting with 8: 2 hexanes: ethyl acetate) to give the title compound as pale yellow oil (189.0 mg, 99percent). HRMS m/z Calculated: 137.0602; Found: 137.0575
The resultig acetylated product (3.0 g) was stirred together with 0.3 g of 10percent palladium-carbon and 50 ml of ethanol at 60° C. for 4 hours in an atmosphere of hydrogen to give 2.0 g of white crystals. The crystals were hydrolyzed in a customary manner to give 1.0 g (total yield 41percent) of the desired product as a brown liquid.
Representative compounds of formula (I) include5-hydroxybenzofuran,6-hydroxybenzofuran,2,3-dihydro-6-hydroxybenzofuran,3-methyl-6-hydroxybenzofuran,2,3-dimethyl-6-hydroxybenzofuran,2,3-dihydro-3-methyl-6-hydroxybenzofuran and2-methyl-5-hydroxybenzofuran.
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