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

2-Furancarbonyl chloride, 5-(chloromethyl)- (9CI)

105850-77-9

64-17-5

ETHYL 5-(CHLOROMETHYL)-2-FURANCARBOXYLATE

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.

50-00-0 Synthesis

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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

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64-17-5 Synthesis

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References

1623-88-7 Synthesis