Reacción #1404

Ecuación de reacción

potassium fluoride

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

H2O

→

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

Disolventes

N,N-dimethylformamide

Condiciones de reacción

Tratamiento posterior

1. 1
   Otrothe solvent was removed in vacuo
2. 2
   Otrothe residue was partitioned between water and ethyl acetate
3. 3
   Extracciónthe aqueous layer was extracted twice with ethyl acetate
4. 4
   Extracciónthe combined extract
5. 5
   Secadowas dried (magnesium sulfate)
6. 6
   Otrowas evaporated
7. 7
   OtroPurification by flash chromatography
8. 8
   Lavadoeluting with 4:1 hexanes/ethyl acetate
9. 9
   Otroprovided a clear colorless oil

Procedimiento

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.

Fuente