反応 #1197360

反応方程式

tetra n-butylammonium fluoride

ether

2-(1-methylethyl)-5,9,13-trimethyl-1-trimethylsiloxy-2,4,8,12-cyclotetradecatetraen-1-carbonitrile

→

2-(1-methylethyl)-5,9,13-trimethyl-2,4,8,12-cyclotetradecatetraen-1-one

収率 85.0%

溶媒

tetrahydrofuran

tetrahydrofuran

反応条件

後処理

1. 1
   その他Most of the tetrahydrofuran was removed in vacuo
2. 2
   workup.DISSOLUTIONthe residue was dissolved in ethyl ether
3. 3
   乾燥The ether layer was dried over MgSO4
4. 4
   ろ過filtered
5. 5
   濃縮concentrated

実験手順

The above cyanohydrine trimethylsily ether compound, 2-(1-methylethyl)-5,9,13-trimethyl-1-trimethylsiloxy-2,4,8,12-cyclotetradecatetraen-1-carbonitrile (657 mg, 1.7 mmol) was dissolved in 10% aqueous tetrahydrofuran (10 ml). To the solution on an ice-water bath was added a solution of 1M tetra n-butylammonium fluoride in tetrahydrofuran (0.02 ml), and the mixture was stirred and then allowed to stand at room temperature for 2 days. Most of the tetrahydrofuran was removed in vacuo and the residue was dissolved in ethyl ether. The ether layer was dried over MgSO4, filtered, concentrated, and subjected to silica gel column chromatography (solvent: n-hexane/ethyl acetate=30:1) to obtain the ketone compound, 2-(1-methylethyl)-5,9,13-trimethyl-2,4,8,12-cyclotetradecatetraen-1-one (411 mg, 85%).

出典