Sulfuric Acid → 1-(Thiophen-3-yl)cyclopropan-1-ol

Reaktionsgleichung

C(O[C:4]([C:6]1[CH:10]=[CH:9][S:8][CH:7]=1)=[O:5])C.[CH2:11]([Mg]Br)[CH3:12].S(=O)(=O)(O)O>C(OCC)C>[S:8]1[CH:9]=[CH:10][C:6]([C:4]2([OH:5])[CH2:12][CH2:11]2)=[CH:7]1

Komponenten

Versuchsvorschrift

1.37 ml (10.00 mmol) ethylthiophene-3-carboxylate and 0.29 ml (1.00 mmol)titanium tetra-isopropyloxide are placed in 5 ml diethyl ether, 21.20 ml (21.20 mmol) ethylmagnesium bromide (Grignard reagent in tetrahydrofuran) in 15 ml diethyl ether are added dropwise within 1 hour, while the temperature should not rise above 20° C. The reaction mixture is stirred for 1.5 hours, then hydrolysed with 10% sulphuric acid. The aqueous phase is extracted with diethyl ether, the combined organic phases are dried and evaporated to dryness. The residue is purified by chromatography. Yield: 0.330 g (24% of theoretical)