
ETHYL 5-(CHLOROMETHYL)-2-FURANCARBOXYLATE synthesis
- Product Name:ETHYL 5-(CHLOROMETHYL)-2-FURANCARBOXYLATE
- CAS Number:2528-00-9
- Molecular formula:C8H9ClO3
- Molecular Weight:188.61

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2528-00-9
Volatiles were removed by distillation under reduced pressure at room temperature and the crude product 5-(chloromethyl)-2-furancarbonyl chloride (4, 2.90 g) was dissolved in anhydrous ethanol (20 mL). The resulting clarified yellow solution was reacted at 50 °C with continuous stirring for 6 hours. Upon completion of the reaction, the solvent was removed by rotary evaporator and the resulting residue was purified by column chromatography using dichloromethane/hexane (1:1 to 3:1 gradient) as eluent to afford the target product, ethyl 5-(chloromethyl)furan-2-carboxylate (5), as a colorless oil (2.390 g, 82% yield). The structure of the product was confirmed by 1H NMR (300 MHz, CDCl3) and 13C NMR (75 MHz, CDCl3): 1H NMR δ 7.06 (d, J = 3.5 Hz, 1H), 6.44 (d, J = 3.5 Hz, 1H), 4.55 (s, 2H), 4.31 (q, J = 7.1 Hz, 2H), 1.32 (t, J = 7.1 Hz, 3H); 13C NMR δ 158.35, 153.96, 145.02, 118.54, 111.37, 61.10, 36.68, 14.26.
Yield: 98%
Reaction Conditions:
with hydrogenchloride;zinc(II) chloride in dichloromethane at 35;
Steps:
1
Example 1; Ethyl 5-chloromethylfuran-2-carboxylate; To a solution of 100 g (0.71 M) of ethyl 2-furoate in 250 ml of 5 dichloromethane are added 30.6 g (1.02 M) of paraformaldehyde and 25.4 g(0.19 M) of zinc chloride. Gaseous hydrogen chloride is passed into the reaction medium. An exothermic reaction is observed, and the temperature reaches350C. The evolution of gas is maintained up to the end of the reaction, which is monitored by thin-layer chromatography (TLC). The product obtained is then o purified by chromatography on silica using dichloromethane as eluent, to give134.6 g of ethyl 5-chloromethylfuran-2-carboxylate in the form of a colourless oil. EPO
References:
MERCK PATENT GMBH WO2007/14619, 2007, A1 Location in patent:Page/Page column 26-27

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