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To a solution of tetrahydro-3-furancarboxylic acid (20.00 g, 172 mmol) in MeOH (350 mL) was added sulfuric acid (27.54 mL, 517 mmol). The reaction was heated to reflux for 18 h. The reaction was then cooled to rt and concentrated. The residue was partitioned between water (500 mL) and DCM (200 mL). The phases were separated and the aqueous fraction was extracted with DCM (200 mL). The combined organic fractions were washed with saturated aqueous NaHCO3 (200 mL) and brine (200 mL), dried over Na2SO4, filtered, and concentrated to afford methyl tetrahydro-3-furancarboxylate (15.0 g, 67percent yield) as a pale yellow oil. 1H NMR (400 MHz, DMSO-d) δ ppm 3.85 (t, J=8.4 Hz, 1H), 3.77-3.66 (m, 3H), 3.62 (s, 3H), 3.07-3.22 (m, 1H), 1.97-2.12 (m, 2H).
Reference：
[1] Journal of Organic Chemistry, 1996, vol. 61, # 8, p. 2690 - 2694
[2] Patent: US2018/201610, 2018, A1, . Location in patent: Paragraph 0076; 0077
[3] Advanced Synthesis and Catalysis, 2010, vol. 352, # 2-3, p. 463 - 477
(S)-N-(2,6-Dimethoxyphenyl)tetrahydrofuran-3-carboxamide and (R)-N-(2,6-dimethoxyphenyl)tetrahydrofuran-3-carboxamide, Example 7.1 (1021) An ice-cooled solution of tetrahydro-3-furoic acid (Sigma-Aldrich, 3.0 g, 26.1 mmol) in DMF (52 mL) was treated with TEA (10.9 mL, 78 mmol) via syringe followed by HATU (10.9 g, 28.7 mmol) directly. After 5 min, <strong>[2734-70-5]2,6-dimethoxyaniline</strong> (Amfinecom Inc., 4.0 g, 26.1 mmol) was added. The resulting orange solution was warmed to RT and stirred for 60 min. The mixture was then partitioned between brine (100 mL) and EtOAc (4×). The combined organic layers were dried over anhydrous magnesium sulfate and concentrated. The residue was purified by silica gel chromatography (eluent: 0-100% EtOAc in hexanes) to provide 7.1 (2.50 g, 38% yield) as a white solid. LCMS-ESI (pos) m/z: 252.2 (M+H)+.
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