تفاعل #1404

معادلة التفاعل

potassium fluoride

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

H2O

→

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

المذيبات

N,N-dimethylformamide

ظروف التفاعل

المعالجة

1. 1
   أخرىthe solvent was removed in vacuo
2. 2
   أخرىthe residue was partitioned between water and ethyl acetate
3. 3
   استخلاصthe aqueous layer was extracted twice with ethyl acetate
4. 4
   استخلاصthe combined extract
5. 5
   تجفيفwas dried (magnesium sulfate)
6. 6
   أخرىwas evaporated
7. 7
   أخرىPurification by flash chromatography
8. 8
   غسيلeluting with 4:1 hexanes/ethyl acetate
9. 9
   أخرىprovided a clear colorless oil

الإجراء التجريبي

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.

المصدر