Dimethylformamide → HCID 59648590, compound

Temperature

-78 °C

Under N2, a solution of 3-methyl-2-furoic acid (2.0 g, 15.9 mmol) in THF (80 mL) was cooled to −78° C. and n-BuLi (1.6 M in hexane) (20.8 mL, 33.3 mmol, 2.1 equiv) was added dropwise. The mixture was kept for 30 min at −78° C., then a solution of DMF (6.11 mL, 79.4 mmol, 5 equiv) in THF (20 mL) was added. After being stirred for 3 h at −78° C., the reaction mixture was allowed to warm to rt. The reaction was quenched with saturated aqueous ammonium chloride then the reaction mixture was partitioned between water and ether. The ether layer was washed with water, and then dried over sodium sulfate, filtered, and the solvent was evaporated. The residue was purified by chromatography over silica gel (0 to 30% EtOAc in heptane over 30 min) to give 5-formyl-3-methyl-2-furoic acid (0.9 g, 37%). 1H NMR (400 MHz, CD3OD) δ ppm 2.39 (s, 3H) 7.29 (s, 1H) 9.67 (s, 1H).

1. temperatureto warm to rt
2. customThe reaction was quenched with saturated aqueous ammonium chloride
3. customthe reaction mixture was partitioned between water and ether
4. washThe ether layer was washed with water
5. dry with materialdried over sodium sulfate
6. filtrationfiltered
7. customthe solvent was evaporated
8. customThe residue was purified by chromatography over silica gel (0 to 30% EtOAc in heptane over 30 min)

ORD record

ord-56b8e69a50ce4c399bea60c1a4d8b576

Source dataset

uspto-grants-2011_02

DOI

10.6084/m9.figshare.5104873.v1

Patent number

US07884124B2