METHYL 5-METHYLBENZOFURAN-2-CARBOXYLATE synthesis

6synthesis methods

Product Name:METHYL 5-METHYLBENZOFURAN-2-CARBOXYLATE
CAS Number:82788-34-9
Molecular formula:C11H10O3
Molecular Weight:190.2

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Yield:82788-34-9 42%

Reaction Conditions:

with Bu₄NBr;potassium carbonate in 4-(dicyanomethylene)-2-methyl-6-(p-dimethylaminostyryl)-4H-pyran;toluene;

Steps:

436.1 Example 436

Step 1: Methyl-5-methyl-benzofuran-2-carboxylate (583) A stirring suspension of 5-methylsalicylaldehyde (1.0 mg, 7.5 mmol), K₂CO₃(1.55 g, 11.0 mmol), and Bu₄NBr (322 mg, 1 mmol) in toluene (30 ml) was treated with dimethylbromomalo-nate (1.06 ml, 8.0 mmol). The suspension was heated to reflux with a Dean-Stark trap for 20 h. The brown suspension was cooled to 25° C. and concentrated in vacuo. The residue was taken in DCM and filtered. The filtrate was washed with H₂O, 1N NaOH and brine. The organic layer was dried over magnesium sulfate, filtered and concentrated. The crude residue was purified by column chromatography (10% ethyl acetate/hexane) to afford the title compound 583 (600 mg, 42% yield). LRMS: 190.2 (Calc.); 191.1 (found).

References:

US2004/142953,2004,A1