3-Furancarboxylic acid, 2,5-dimethyl-, methyl ester → (2,5-Dimethylfuran-3-yl)methanol

Temperature

0 °C

To a 0° C. solution of methyl 2,5-dimethyl-3-furanoate (2.0 g, 13.0 mmol) in THF (130 mL) under N2 was added lithium aluminum hydride (39 mL of a 1.0 M solution in THF, 38.9 mmol) dropwise. The reaction was stirred at 0° C. for 3.5 h, at which time it was quenched cautiously with saturated aqueous Na2SO4 solution and allowed to warm to room temperature. The reaction mixture was filtered and rinsed with ethyl acetate, the filtrate was diluted with more ethyl acetate and the layers separated. The organic layer was washed with saturated aqueous NH4Cl, water and brine and dried over Na2SO4. The solution was filtered and concentrated to afford the title compound as a clear liquid (1.54 g, 12.2 mmol, 94%). 1H NMR (300 MHz, DMSO-d6): δ 5.93 (s, 1H); 4.18 (s, 2H); 2.17 (s, 3H); 2.15 (s, 3H).

1. customwas quenched cautiously with saturated aqueous Na2SO4 solution
2. temperatureto warm to room temperature
3. filtrationThe reaction mixture was filtered
4. washrinsed with ethyl acetate
5. additionthe filtrate was diluted with more ethyl acetate
6. customthe layers separated
7. washThe organic layer was washed with saturated aqueous NH4Cl, water and brine
8. dry with materialdried over Na2SO4
9. filtrationThe solution was filtered
10. concentrationconcentrated

ORD record

ord-a082dcb31e2f4069aed6afecb3ac8471

Source dataset

uspto-grants-2004_05

DOI

10.6084/m9.figshare.5104873.v1

Patent number

US06730675B2