Hydrochloric Acid → O-ethyl S-(2,5-dimethyl-3-furyl) thiocarbonate

To a mixture of ethyl chloroformate (0.86 g, 7.9 mmol) and 2,5-dimethyl-furan-3-thiol (1 g, 7.8 mmol) in methyl ethyl ketone (10 ml) was added triethylamine (0.8 g, 7.9 mmol). The mixture was cooled in ice and stirred for 3 hours. After reaching room temperature water (10 g) was added to the mixture to dissolve the triethylammonium chloride which was formed during the reaction. Concentrated hydrochloric acid (2 g) was added to neutralise the excess triethylamine. The organic layer was separated and washed with a saturated sodium hydrogen carbonate solution (10 g), water (10 g) and finally a sodium sulphate solution (10 g). After evaporation of the solvent the residue was analysed and confined by NMR spectroscopy as O-ethyl S-(2,5-dimethyl-3-furyl) thiocarbonate yield 89% (1.4 g, 7 mmol) purity 91%.

1. temperatureThe mixture was cooled in ice
2. customAfter reaching room temperature
3. additionwas added to the mixture
4. customwas formed during the reaction
5. customThe organic layer was separated
6. washwashed with a saturated sodium hydrogen carbonate solution (10 g), water (10 g)
7. customAfter evaporation of the solvent the residue

ORD record

ord-0667694cf6c1464d972c87b8734fcae2

Source dataset

uspto-grants-2005_02

DOI

10.6084/m9.figshare.5104873.v1

Patent number

US06852350B2