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

Intermediate 4

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

sodium hydroxide

→

title compound

수율 87.8%

5-[2-methyl-5-(trimethylsilyl)phenoxy]furan-2-carboxylic acid

수율 87.8%

용매

methyl alcohol

water

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후처리

1. 1
   농축The resulting mixture was concentrated under reduced pressure
2. 2
   추출extracted into diethyl ether (1×20 mL)
3. 3
   추출extracted with ethyl acetate (2×25 mL)
4. 4
   건조The organic extracts were dried (magnesium sulphate)
5. 5
   농축concentrated under reduced pressure

실험 절차

To a solution of methyl 5-[2-methyl-5-(trimethylsilyl)phenoxy]furan-2-carboxylate (Intermediate 4; 217 mg, 0.71 mmol) in methyl alcohol (3 mL) at room temperature was added a solution of sodium hydroxide (126 mg) in water (1 mL) and the reaction stirred for 18 hours. The resulting mixture was concentrated under reduced pressure, the residue taken up in water and extracted into diethyl ether (1×20 mL). The aqueous layer was acidified with hydrochloric acid (1 M) and extracted with ethyl acetate (2×25 mL). The organic extracts were dried (magnesium sulphate) and concentrated under reduced pressure to give the title compound as a colourless powder (181 mg, 87%). Rf=0.21 (9:1, dichloromethane-methyl alcohol). LCMS Rt=4.33 minutes, m/z=291 (MH+).

출처