Dimethylformamide → 5-propylfuran-2-carbaldehyde

To a solution of 13.04 g (0.118 mol) of 2-propylfuran in 800 mL of ether cooled at 0° C. with stirring under nitrogen was added dropwise 52 mL (0.130 mol) of 2.5M n-butyllithium. The reaction mixture was allowed to warm to room temperature and then refluxed for 40 min. The reaction mixture was cooled to -60° C., 10.1 mL (0.130 mol) of DMF in 10 mL of ether was added, and the resulting mixture was stirred at -60° C. for 45 min, and warmed to room temperature. The above mixture was quenched with 10 mL of saturated aqueous ammonium chloride, diluted with water to form a clear aqueous layer, and the organic layer was washed with water, and brine. The organic layer was dried over anhydrous magnesium sulfate, treated with a small amount of a charcoal, filtered, and concentrated to yield 13.95 g of a crude oil. The kughelrohr distillation of this oil (75°-105° C.) afforded 10.5 g (64.5%) of 5-propyl-2-furancarboxaldehyde.

1. temperaturerefluxed for 40 min
2. temperatureThe reaction mixture was cooled to -60° C.
3. stirringthe resulting mixture was stirred at -60° C. for 45 min
4. temperaturewarmed to room temperature
5. customThe above mixture was quenched with 10 mL of saturated aqueous ammonium chloride
6. additiondiluted with water
7. customto form a clear aqueous layer
8. washthe organic layer was washed with water, and brine
9. dry with materialThe organic layer was dried over anhydrous magnesium sulfate
10. additiontreated with a small amount of a charcoal
11. filtrationfiltered
12. concentrationconcentrated
13. customto yield 13.95 g of a crude oil
14. distillationThe kughelrohr distillation of this oil (75°-105° C.)

ORD record

ord-77f769851a2742a6b3fb6d0ec1649bdd

Source dataset

uspto-grants-1997_09

DOI

10.6084/m9.figshare.5104873.v1

Patent number

US05665763