تفاعل #6617

معادلة التفاعل

product

1-((trimethylsilyl)ethynyl)-2-(4-fluoro-3-methylphenyl)-4,4,6,6-tetramethylcyclohexene

acetic acid

tetrabutylammonium fluoride

→

1-(ethynyl)-2-(4-fluoro-3-methylphenyl)-4,4,6,6-tetramethyl-1-cyclohexene

المردود 98.0%

المذيبات

THF

THF

ether

ظروف التفاعل

المعالجة

1. 1
   غسيلwashed with saturated ammonium chloride solution
2. 2
   تجفيفThe ether fraction is dried over MgSO4
3. 3
   أخرىthe solvent is removed under reduced pressure
4. 4
   أخرىPurification by silica gel chromatography (100% hexane)

الإجراء التجريبي

To a solution of the product from Example 1, Step D above (5 g, 14.6 mmol), and acetic acid (1.3 ml, 21.9 mmol) in THF (15 ml) at 0° C. is added tetrabutylammonium fluoride in THF (1M, 21.9 ml, 21.9 mmol). The resulting solution is stirred for 12 hours at room temperature, diluted with ether and washed with saturated ammonium chloride solution. The ether fraction is dried over MgSO4, and the solvent is removed under reduced pressure. Purification by silica gel chromatography (100% hexane) provides 3.9 g (98%) of 1-(ethynyl)-2-(4-fluoro-3-methylphenyl)-4,4,6,6-tetramethyl-1-cyclohexene: 1H NMR δ=1.0 (s,6), 1.22 (s,6), 1.45 (s,2), 2.15 (s,2), 2.25 (s,3), 2.75 (s,1), 6.95 (t,1), 7.15 (m,2).

المصدر