Methanol → Methyl tetrahydrofuran-3-carboxylate

To a solution of tetrahydro-3-furancarboxylic acid (10.00 g, 86.0 mmol) in MeOH (172 mL) was added sulfuric acid (13.8 mL, 258 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 (10.1 g, 78 mmol, 90% yield) as a pale yellow oil. 1H NMR (400 MHz, CDCl3) δ ppm 3.99 (t, J=8.4 Hz, 1H), 3.86-3.95 (m, 2H), 3.76-3.86 (m, 1H), 3.71 (s, 3H), 3.01-3.18 (m, 1H), 2.03-2.32 (m, 2H).

1. temperatureThe reaction was heated
2. temperatureto reflux for 18 h
3. concentrationconcentrated
4. customThe residue was partitioned between water (500 mL) and DCM (200 mL)
5. customThe phases were separated
6. extractionthe aqueous fraction was extracted with DCM (200 mL)
7. washThe combined organic fractions were washed with saturated aqueous NaHCO3 (200 mL) and brine (200 mL)
8. dry with materialdried over Na2SO4
9. filtrationfiltered
10. concentrationconcentrated

ORD record

ord-76773f5d43b844d1a721d8945af2df88

Source dataset

uspto-grants-2014_02

DOI

10.6084/m9.figshare.5104873.v1

Patent number

US08642759B2