Water → Ethyl 5-(hydroxymethyl)thiophene-2-carboxylate

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[S:1]1[C:5]([C:6](OCC)=[O:7])=[CH:4][CH:3]=[C:2]1[C:11]([O:13][CH2:14][CH3:15])=[O:12].[BH4-].[Na+].O>C(O)C>[OH:7][CH2:6][C:5]1[S:1][C:2]([C:11]([O:13][CH2:14][CH3:15])=[O:12])=[CH:3][CH:4]=1

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실험 절차

Diethyl 2,5-thiophenedicarboxylate (1.14 g, 5 mmol) synthesized in Production Example 71 was dissolved in ethanol, and sodium tetrahydroborate (113 mg, 3 mmol) was added thereto. The mixture was stirred for 3 days at a room temperature. After the completion of the reaction was confirmed by HPLC, water was added to the mixture, and the resulting mixture was concentrated under a reduced pressure. The residue was dissolved in ethyl acetate, washed with water and a saturated sodium chloride aqueous solution, and then dried over anhydrous magnesium sulfate, and the solvent was distilled off. The resulting residue was purified by flash column chromatography (Yamazen Hi-Flash column, silica gel, hexane/ethyl acetate (volume ratio)=3:2) to give the title compound (491 mg, 52.7%) as an oily substance.