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

Participants

Reaction Conditions

Reaction Steps

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.

Provenance & Evidence