반응 #83575

반응 방정식

4-(2-trimethylsilylethinyl)-phenylacetic acid methyl ester

tetrabutylammonium fluoride

→

4-ethinylphenylacetic acid methyl ester

수율 79.2%

용매

tetrahydrofuran

tetrahydrofuran

반응 조건

후처리

1. 1
   농축concentrated by evaporation
2. 2
   기타the organic phase is dried on sodium sulfate
3. 3
   농축concentrated by evaporation
4. 4
   기타the residue is chromatographed on silica gel with hexane/0-7% ethyl acetate

실험 절차

A solution of 10 g of 4-(2-trimethylsilylethinyl)-phenylacetic acid methyl ester in 950 ml of tetrahydrofuran is mixed at 0° C. with 45 ml of a 1-molar solution of tetrabutylammonium fluoride in tetrahydrofuran. The reaction mixture is stirred for 15 minutes at 0° C. and for 2 hours at room temperature and then concentrated by evaporation. The residue is spread between water and ethyl acetate, the organic phase is dried on sodium sulfate, concentrated by evaporation and the residue is chromatographed on silica gel with hexane/0-7% ethyl acetate. 5.6 g of 4-ethinylphenylacetic acid methyl ester is obtained as oily crude product.

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