Acetyl chloride → Methyl (furan-3-yl)acetate

Temperature

0 °C

A mixture of 3-formylfuran (5.0 g), methyl (methylthiomethyl)sulphoxide (7.lg) and Triton B [(40 weight % solution of benzyltrimethylammonium hydroxide in methanol) 4.8 g] in THF (7 ml) was heated under reflux for 5 hours. After cooling, it was poured into water and extracted with ether. The extracts were washed with water (× 3) and then with aqueous sodium chloride, then dried and concentrated to give a brown oil (4.Og), IR (film) 1610, 1060 cm-1 . Acetyl chloride (1.4 ml) was added carefully with stirring to dry methanol (25 ml), cooled to 0° C. Following the addition, the resulting mixture was allowed to warm to room temPerature, and part of the brown oil (2.0g) was added to it in one portion with stirring. After 30 minutes, the resulting mixture was heated at 100° C. under reflux for 2 hours, then allowed to cool, poured into water and extracted with ether. The extracts were washed successively with water (× 3), aqueous sodium bicarbonate and aqueous sodium chloride, then dried, concentrated, and eluted through a short column of silica gel using a 1:1 mixture of ether and petrol to give methyl (3-furyl)acetate (1.3 g, 36% yield from 3-formylfuran) as a yellow oil, IR (film) 1736 cm-1.

1. temperaturewas heated
2. temperatureunder reflux for 5 hours
3. temperatureAfter cooling
4. extractionextracted with ether
5. washThe extracts were washed with water (× 3)
6. dry with materialwith aqueous sodium chloride, then dried
7. concentrationconcentrated
8. customto give a brown oil (4.Og), IR (film) 1610, 1060 cm-1
9. additionthe addition
10. temperatureto warm to room temPerature
11. temperaturethe resulting mixture was heated at 100° C.
12. temperatureunder reflux for 2 hours
13. temperatureto cool
14. extractionextracted with ether
15. washThe extracts were washed successively with water (× 3), aqueous sodium bicarbonate and aqueous sodium chloride
16. customdried
17. concentrationconcentrated
18. washeluted through a short column of silica gel using
19. additiona 1:1 mixture of ether and petrol

ORD record

ord-302f6dc301df45d2ad6e145baca28671

Source dataset

uspto-grants-1992_11

DOI

10.6084/m9.figshare.5104873.v1

Patent number

US05160364