8-(4-Fluorophenyl)-1,4-dioxaspiro[4.5]decane → 4-(4-Fluorophenyl)cyclohexan-1-one

HRID 1025677Notes

Reaction equation

HRID 1025677 reaction equation
[F:1][C:2]1[CH:7]=[CH:6][C:5]([CH:8]2[CH2:17][CH2:16][C:11]3(OCC[O:12]3)[CH2:10][CH2:9]2)=[CH:4][CH:3]=1>C1(C)C=CC=CC=1.C1COCC1.OS(O)(=O)=O.O>[F:1][C:2]1[CH:3]=[CH:4][C:5]([CH:8]2[CH2:9][CH2:10][C:11](=[O:12])[CH2:16][CH2:17]2)=[CH:6][CH:7]=1

Participants

6

Reactant 1

HCID 128344048-(4-Fluorophenyl)-1,4-dioxaspiro[4.5]decane

Product 1

HCID 128343224-(4-Fluorophenyl)cyclohexan-1-oneYield 86%

Reagents, catalysts & solvents 4

HCID 962WaterSolventHCID 1118Sulfuric AcidSolventHCID 1140TolueneSolventHCID 8028TetrahydrofuranSolvent

Procedure

A solution of the intermediate from step B (8.6 g, 36.5 mmol) in toluene (40 mL), THF (20 mL) and 10% H2SO4 in water (25 mL) was stirred at reflux overnight. After cooling to room temperature, the organic layer was separated, washed with brine, dried over MgSO4 and concentrated. Flash chromatography on silica gel eluting with 5% and then 10% EtOAc in hexanes provided the title compound (6.0 g, 86%) as an oil. MS calculated (M+H)+ 193, found 193.

Workup

  1. temperatureat reflux overnight
  2. customthe organic layer was separated
  3. washwashed with brine
  4. dry with materialdried over MgSO4
  5. concentrationconcentrated

Sources & evidence

ORD record
ord-d73e74edae524c2fbe05d8be1d6eaac7
Source dataset
uspto-grants-2014_05
Patent number
US08729063B2

Reaction notes

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