Methane, dichloromethoxy- → 7-Methoxy-2-methyl-1-benzofuran-4-carbaldehyde

Participants

Reaction Steps

To a well stirred solution of 7-methoxy-2-methylbenzo[b]furan (from step 2) (6.5 g, 40.07 mmol) in DCM (70.0 mL) was added stannous chloride (17.7 g, 68.26 mmol) followed by slow addition of 1,1-dichloromethyl methyl ether (4.6 g, 40.07 mmol) at −10-0° C. and stirred for 1-2 hrs. Ice cold water (100 mL) was added with vigorous stirring, the organic layer was separated and washed with water (2×50 mL) and dried over anhydrous sodium sulfate. Removal of solvent gave crude product (7.0 g). The crude product was purified by silica gel column using petroleum ether:ethyl acetate (9:1) as an eluent to afford the product as pale yellow oil (2.3 g).

Provenance & Evidence