反応 #2304278

反応方程式

methyl 5-bromo-2-furoate

hydrochloric acid

5-trimethylsilyl-2-methylphenol

Intermediate 3

5-trimethylsilyl-2-methylphenol

potassium tert-butoxide

→

title compound

収率 57.0%

Methyl 5-[2-methyl-5-(trimethylsilyl)phenoxy]furan-2-carboxylate

収率 57.0%

溶媒

water

THF

反応条件

後処理

1. 1
   温度the reaction heated
2. 2
   温度at reflux for 1.5 hours
3. 3
   濃縮concentrated under reduced pressure
4. 4
   温度heated at 85° C. for 18 hours
5. 5
   温度to cool to room temperature
6. 6
   抽出The mixture was extracted with diethyl ether (3×30 mL)
7. 7
   乾燥the combined organic extracts were dried (magnesium sulphate)
8. 8
   濃縮concentrated under reduced pressure
9. 9
   その他purified by column chromatography (SiO2; light petroleum to 95:5 light petroleum-diethyl ether)

実験手順

To a solution of 5-trimethylsilyl-2-methylphenol (Intermediate 3; 653 mg, 3.6 mmol) in THF was added potassium tert-butoxide (407 mg, 3.6 mmol) and the reaction heated at reflux for 1.5 hours. The resulting solution was allowed to cool to room temperature and concentrated under reduced pressure. The residue was taken up in dimethyl sulphoxide (10 mL), treated with methyl 5-bromo-2-furoate (632 mg, 3.1 mmol) and heated at 85° C. for 18 hours. The dark brown mixture was allowed to cool to room temperature, diluted with water (10 mL) and then acidified by the addition of hydrochloric acid (1 M). The mixture was extracted with diethyl ether (3×30 mL) and the combined organic extracts were dried (magnesium sulphate), concentrated under reduced pressure and purified by column chromatography (SiO2; light petroleum to 95:5 light petroleum-diethyl ether) to give the title compound as a colourless oil (534 mg, 57%). Rf=0.21 (9:1 light petroleum-diethyl ether). LCMS Rt=4.9 mins, m/z=305 (MH+).

出典