ChemicalBook CAS DataBase List ETHYL 5-(CHLOROMETHYL)-2-FURANCARBOXYLATE

ETHYL 5-(CHLOROMETHYL)-2-FURANCARBOXYLATE synthesis

6synthesis methods

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

50-00-0 Synthesis

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ETHYL 5-(CHLOROMETHYL)-2-FURANCARBOXYLATE

2528-00-9
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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 Yield: 98%.¹H NMR (200 MHz/DMSO-d6) δ (ppm): 1.28 (t, 3H); 4.27 (d, 2H); 4.51 (s, 2H);6.39 (d, 1 H); 7.02 (d, 1 H).

References:

MERCK PATENT GMBH WO2007/14619, 2007, A1 Location in patent:Page/Page column 26-27