1,4-Dioxaspiro[4.5]decan-8-one → 8-Cyclohexyl-1,4-dioxaspiro[4.5]decan-8-ol

HRID 1816762ノート

反応式

HRID 1816762 の反応式
[Cl-].[Cl-].[Cl-].[Cs+].[Cs+].[Cs+].[O:7]1[C:11]2([CH2:16][CH2:15][C:14](=[O:17])[CH2:13][CH2:12]2)[O:10][CH2:9][CH2:8]1.[CH:18]1([Mg]Cl)[CH2:23][CH2:22][CH2:21][CH2:20][CH2:19]1>O1CCCC1>[CH:18]1([C:14]2([OH:17])[CH2:13][CH2:12][C:11]3([O:10][CH2:9][CH2:8][O:7]3)[CH2:16][CH2:15]2)[CH2:23][CH2:22][CH2:21][CH2:20][CH2:19]1

参加物

5

反応物 3

HCID 5674151,4-Dioxaspiro[4.5]decan-8-oneHCID 20975861Cesium trichlorideHCID 178478990HCID 178478990、化合物

生成物 1

HCID 224947648-Cyclohexyl-1,4-dioxaspiro[4.5]decan-8-ol

試薬・触媒・溶媒 1

HCID 8028Tetrahydrofuran溶媒

実験手順

A mixture of cesium trichloride (5.0 g) in tetrahydrofuran (45 ml) was stirred at room temperature for 6 hours. 1,4-Dioxaspiro[4.5]decan-8-one (1.4 g) was added to the solution and stirred at room temperature for 1 hour. To the solution was added dropwise with stirring cyclohexylmagnesium chloride (2.0M solution in diethyl ether) (6.7 ml) at 0° C. The reaction mixture was quenched with 10% acetic acid aqueous solution. Diethyl ether was added to the solution. The organic layer was taken, washed with brine, sodium hydrogen carbonate solution, brine and dried over magnesium sulfate. The magnesium sulfate was filtered off, and the filtrate was concentrated under reduced pressure. The residue was purified by silica gel chromatography to give 8-cyclohexyl-1,4-dioxaspiro[4.5]decan-8-ol (1.266 g).

後処理

  1. stirringstirred at room temperature for 1 hour
  2. customThe reaction mixture was quenched with 10% acetic acid aqueous solution
  3. additionDiethyl ether was added to the solution
  4. washwashed with brine, sodium hydrogen carbonate solution, brine
  5. dry with materialdried over magnesium sulfate
  6. filtrationThe magnesium sulfate was filtered off
  7. concentrationthe filtrate was concentrated under reduced pressure
  8. customThe residue was purified by silica gel chromatography

出典と根拠

ORDレコード
ord-686e94403b054095a9676d0ea6e6770e
出典データセット
uspto-grants-2005_04
特許番号
US06884868B1

反応ノート

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