Methyl iodide → Ethyl 2-methoxymethyl-2,3-dihydrobenzofuran-5-carboxylate

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Reaction Conditions

Reaction Steps

A solution of 2.5 g (11.26 mmole) ethyl 2-hydroxymethyl-2,3-dihydrobenzofuran-5-carboxylate in 50 ml tetrahydrofuran was cooled under nitrogen to 0° C. and 595 mg (12.38 mmole) of a 50% by weight dispersion of sodium hydride in oil was added in portions. The mixture was stirred to 0° C. for 15 minutes, then a solution of 1.756 g (12.38 mmole) methyl iodide in 30 ml tetrahydrofuran was added dropwise. The resulting mixture was allowed to warm to room temperature and stirred overnight. The mixture was concentrated in vacuo, the residue partitioned between ethyl ether and water. The ether extracts were combined, washed with brine, dried (MgSO4) and the solvent evaporated in vacuo to yield 2.28 g of product as an oil. 1H-NMR(CDCl3) showed singlet at 3.4 ppm, consistent with the presence of a CH2OCH3 group.

Provenance & Evidence