Реакция #1404

Уравнение реакции

potassium fluoride

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

H2O

→

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

Растворители

N,N-dimethylformamide

Условия реакции

Обработка

1. 1
   Другоеthe solvent was removed in vacuo
2. 2
   Другоеthe residue was partitioned between water and ethyl acetate
3. 3
   Экстракцияthe aqueous layer was extracted twice with ethyl acetate
4. 4
   Экстракцияthe combined extract
5. 5
   Сушкаwas dried (magnesium sulfate)
6. 6
   Другоеwas evaporated
7. 7
   ДругоеPurification by flash chromatography
8. 8
   Промывкаeluting with 4:1 hexanes/ethyl acetate
9. 9
   Другоеprovided a clear colorless oil

Методика

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.

Источник