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

HRID 1816762Notes

Reaction equation

HRID 1816762 reaction equation
[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

Participants

5

Reactant 3

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

Product 1

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

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

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).

Workup

  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

Sources & evidence

ORD record
ord-686e94403b054095a9676d0ea6e6770e
Source dataset
uspto-grants-2005_04
Patent number
US06884868B1

Reaction notes

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