반응 #823692

반응 방정식

5-methylsalicylaldehyde

K2CO3

dimethylbromomalo-nate

→

title compound 583

수율 42.1%

Methyl-5-methyl-benzofuran-2-carboxylate

수율 42.1%

용매

toluene

반응 조건

후처리

1. 1
   온도The suspension was heated
2. 2
   온도to reflux with a Dean-Stark trap for 20 h
3. 3
   농축concentrated in vacuo
4. 4
   여과filtered
5. 5
   세척The filtrate was washed with H2O, 1N NaOH and brine
6. 6
   건조The organic layer was dried over magnesium sulfate
7. 7
   여과filtered
8. 8
   농축concentrated
9. 9
   기타The crude residue was purified by column chromatography (10% ethyl acetate/hexane)

실험 절차

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).

출처