反応 #6617

反応方程式

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

収率 98.0%

溶媒

THF

THF

ether

反応条件

後処理

1. 1
   洗浄washed with saturated ammonium chloride solution
2. 2
   乾燥The ether fraction is dried over MgSO4
3. 3
   その他the solvent is removed under reduced pressure
4. 4
   その他Purification by silica gel chromatography (100% hexane)

実験手順

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).

出典