Tetrabutylammonium Fluoride → 2-[N-(methoxycarbonylmethyl)carbamoyl]-5-(3-thienylmethoxy)phenol

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A mixture of 1-[N-(methoxycarbonylmethyl)carbamoyl]-2-[2-(trimethylsilyl)ethoxy]methoxy-4-(3-thienylmethoxy)benzene (3.3 g), tetrabutylammonium fluoride (20 mL of a 1 M solution in tetrahydrofuran) and tetrahydrofuran (30 mL) is stirred at ambient temperature for one hour and at reflux for 45 minutes, then it is cooled to ambient temperature and concentrated in vacuo. The resulting residue is partitioned between ethyl acetate (100 mL) and saturated brine (100 mL), and the organic layer is washed with brine (2×50 mL), dried over magnesium sulphate, filtered and concentrated in vacuo. Flash chromatography of the residual oil on silica gel, eluting with a mixture of methanol and dichloromethane (2:98 v/v) gives 2-[N-(methoxycarbonylmethyl)carbamoyl]-5-(3-thienylmethoxy)phenol (2.3 g), in the form of a white solid.

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