Ethanol → HCID 58991874, compound

HRID 2220578Notes

Reaction equation

HRID 2220578 reaction equation
[CH2:1]([O:3][C:4]1[CH:9]=[CH:8][C:7]([C:10]2[CH2:15][CH2:14][CH:13]([CH:16]3[CH2:25][CH2:24][C:19]4([O:23][CH2:22][CH2:21][O:20]4)[CH2:18][CH2:17]3)[CH2:12][CH:11]=2)=[C:6]([F:26])[C:5]=1[F:27])[CH3:2].C([OH:30])C.[OH-].[Na+].OO>C1COCC1.O>[O:23]1[C:19]2([CH2:24][CH2:25][CH:16]([CH:13]3[CH2:14][CH:15]([OH:30])[CH:10]([C:7]4[CH:8]=[CH:9][C:4]([O:3][CH2:1][CH3:2])=[C:5]([F:27])[C:6]=4[F:26])[CH2:11][CH2:12]3)[CH2:17][CH2:18]2)[O:20][CH2:21][CH2:22]1

Participants

7

Reactant 4

HCID 702EthanolHCID 784Hydrogen PeroxideHCID 14798Sodium HydroxideHCID 59773648HCID 59773648, compound

Product 1

HCID 58991874HCID 58991874, compound

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 8028TetrahydrofuranSolvent

Procedure

550 ml (0.55 mol) of borane/THF complex (1 M solution) are added at −5° C. to a solution of 154.0 g (0.41 mol) of 8-[4-(4-ethoxy-2,3-difluorophenyl)-cyclohex-3-enyl]-1,4-dioxaspiro[4.5]decane in 1500 ml of THF, and the reaction mixture is stirred at room temperature for 3 h. 99 ml (1.7 mol) of ethanol, 250 ml (1.0 mol) of aqueous sodium hydroxide solution (16%) and 140 ml (1.6 mol) of aqueous hydrogen peroxide soln. (35%) are added successively to the batch, during which the internal temperature does not exceed 46° C. (ice bath). When the addition is complete, the mixture is refluxed for 2 h, and the solution is cooled, added to water and stirred vigorously. The organic phase is separated off, and the aqueous phase is extracted with MTBE. The combined organic phases are washed with sat. sodium chloride solution and dried using sodium sulfate. The solution is concentrated to dryness, and the crude product is purified by column chromatography (SiO2, toluene:ethyl acetate=8:2), giving 5-(1,4-dioxaspiro[4.5]dec-8-yl)-2-(4-ethoxy-2,3-difluorophenyl)cyclohexanol as colourless, viscous oil.

Workup

  1. addition(35%) are added successively to the batch, during which the internal temperature
  2. customdoes not exceed 46° C.
  3. additionWhen the addition
  4. temperaturethe mixture is refluxed for 2 h
  5. temperaturethe solution is cooled
  6. stirringstirred vigorously
  7. customThe organic phase is separated off
  8. extractionthe aqueous phase is extracted with MTBE
  9. washThe combined organic phases are washed with sat. sodium chloride solution
  10. customdried
  11. concentrationThe solution is concentrated to dryness
  12. customthe crude product is purified by column chromatography (SiO2, toluene:ethyl acetate=8:2)

Sources & evidence

ORD record
ord-706dc40c241a4ca4b9188be1bee98ace
Source dataset
uspto-grants-2008_08
Patent number
US07417157B2

Reaction notes

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