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

HRID 1816347Notes

Reaction equation

HRID 1816347 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.[C:18]1([Mg]Cl)[CH:23]=[CH:22][CH:21]=[CH:20][CH:19]=1>O1CCCC1>[C: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)[CH:23]=[CH:22][CH:21]=[CH:20][CH:19]=1

Participants

5

Reactant 3

HCID 5674151,4-Dioxaspiro[4.5]decan-8-oneHCID 20975861Cesium trichlorideHCID 178478979HCID 178478979, compound

Product 1

HCID 149775528-Phenyl-1,4-dioxaspiro[4.5]decan-8-ol

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

A mixture of cesium trichloride (24.9 g) in tetrahydrofuran (45 ml) was stirred at room temperature for 5 hours. 1,4-Dioxa-spiro[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 phenylmagnesium chloride (3.0M solution in dimethyl ether) (33.7 ml) at 0° C. The reaction mixture was quenched with 10% acetic acid aqueous solution. Dimethyl ether was added to the solution. The organic layer was washed with brine, sodium hydrogen carbonate solution and 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 (3:1 hexane-ethyl acetate elution) to give 8-phenyl-1,4-dioxaspiro[4.5]decan-8-ol (5.94 g).

Workup

  1. stirringstirred at room temperature for 1 hour
  2. customThe reaction mixture was quenched with 10% acetic acid aqueous solution
  3. additionDimethyl ether was added to the solution
  4. washThe organic layer was washed with brine, sodium hydrogen carbonate solution and 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 (3:1 hexane-ethyl acetate elution)

Sources & evidence

ORD record
ord-c5f3c3bde7134e2e8f46dadaa4a5ca4d
Source dataset
uspto-grants-2005_04
Patent number
US06884774B2

Reaction notes

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