반응 #6616

반응 방정식

hydroxy acetylene

1-((trimethylsilyl)ethynyl)-2-(4-fluoro-3-methylphenyl)-4,4,6,6-tetramethyl-cyclohexan-1-ol

Burgess reagent

→

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

수율 67.0%

용매

H2O

acetonitrile

반응 조건

후처리

1. 1
   온도The reaction mixture is heated
2. 2
   온도at reflux for 14 hours
3. 3
   추출The aqueous solution is extracted with ether
4. 4
   세척the combined ether layers are washed with H2O
5. 5
   건조The ether fraction is dried over MgSO4
6. 6
   기타the solvent is removed under reduced pressure
7. 7
   기타Purification by silica gel chromatography (100% hexane)

실험 절차

To a solution of the hydroxy acetylene from Example 1, Step C above (20 g, 55.5 mmol) in acetonitrile (250 ml) is added 20 g (83 mmol) of Burgess reagent. The reaction mixture is heated at reflux for 14 hours, cooled to room temperature and diluted with H2O (1 L). The aqueous solution is extracted with ether and the combined ether layers are washed with H2O. The ether fraction is dried over MgSO4 and the solvent is removed under reduced pressure. Purification by silica gel chromatography (100% hexane) provides 12.7 g (67%) of 1-((trimethylsilyl)ethynyl)-2-(4-fluoro-3-methylphenyl)-4,4,6,6-tetramethylcyclohexene as an oil: 1H NMR δ=0.0 (s,9), 0.95 (s,6), 1.15 (s,6), 1.4 ((s,2), 2.1 (s,2), 2.2 (s,3), 6.85 (t,1), 7.25 (m,2).

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