Reaktion #1404

Reaktionsgleichung

potassium fluoride

3-(3-cyclopentyloxy-4-methoxyphenyl)-3-trimethylsilylethynylcyclohexan-1-one

H2O

→

3-(3-cyclopentyloxy-4-methoxyphenyl)-3-ethynylcyclohexan-1-one

Lösungsmittel

N,N-dimethylformamide

Reaktionsbedingungen

Aufarbeitung

1. 1
   Sonstigethe solvent was removed in vacuo
2. 2
   Sonstigethe residue was partitioned between water and ethyl acetate
3. 3
   Extraktionthe aqueous layer was extracted twice with ethyl acetate
4. 4
   Extraktionthe combined extract
5. 5
   Trocknenwas dried (magnesium sulfate)
6. 6
   Sonstigewas evaporated
7. 7
   SonstigePurification by flash chromatography
8. 8
   Wascheneluting with 4:1 hexanes/ethyl acetate
9. 9
   Sonstigeprovided a clear colorless oil

Vorschrift

A mixture of potassium fluoride (900 mg, 15.6 mmol) and 3-(3-cyclopentyloxy-4-methoxyphenyl)-3-trimethylsilylethynylcyclohexan-1-one (0.3 g, 0.78 mmol) were stirred in dry N,N-dimethylformamide (3 mL) under an argon atmosphere. After 18 h, the solvent was removed in vacuo, the residue was partitioned between water and ethyl acetate, the aqueous layer was extracted twice with ethyl acetate, the combined extract was dried (magnesium sulfate) and was evaporated. Purification by flash chromatography, eluting with 4:1 hexanes/ethyl acetate provided a clear colorless oil. Anal. (C20H24O3.1/10 H2O) calcd: C 76.45, H 7.76; found: C 76.32, H 7.60.

Quelle