Reaction #1404

Reaction equation

potassium fluoride

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

H2O

→

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

Solvents

N,N-dimethylformamide

Conditions

Workup

1. 1
   Otherthe solvent was removed in vacuo
2. 2
   Otherthe residue was partitioned between water and ethyl acetate
3. 3
   Extractionthe aqueous layer was extracted twice with ethyl acetate
4. 4
   Extractionthe combined extract
5. 5
   Dryingwas dried (magnesium sulfate)
6. 6
   Otherwas evaporated
7. 7
   OtherPurification by flash chromatography
8. 8
   Washeluting with 4:1 hexanes/ethyl acetate
9. 9
   Otherprovided a clear colorless oil

Procedure

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.

Source