Ethanol → HCID 58991866, compound

HRID 2220564Notes

Reaction equation

HRID 2220564 reaction equation
[CH2:1]([O:3][C:4]1[CH:9]=[CH:8][C:7]([C:10]2[CH2:19][CH2:18][C:13]3([O:17][CH2:16][CH2:15][O:14]3)[CH2:12][CH:11]=2)=[C:6]([F:20])[C:5]=1[F:21])[CH3:2].C([OH:24])C.[OH-].[Na+].OO>C1COCC1.O>[CH2:1]([O:3][C:4]1[CH:9]=[CH:8][C:7]([CH:10]2[CH2:19][CH2:18][C:13]3([O:14][CH2:15][CH2:16][O:17]3)[CH2:12][CH:11]2[OH:24])=[C:6]([F:20])[C:5]=1[F:21])[CH3:2]

Participants

7

Reactant 4

HCID 702EthanolHCID 784Hydrogen PeroxideHCID 14798Sodium HydroxideHCID 58991877HCID 58991877, compound

Product 1

HCID 58991866HCID 58991866, compound

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 8028TetrahydrofuranSolvent

Procedure

1400 ml (1.40 mol) of borane/THF complex (1 M solution) are added at −7° C. to a solution of 320.0 g (1.08 mol) of 8-(4-ethoxy-2,3-difluorophenyl)-1,4-dioxaspiro[4.5]dec-7-ene in 3000 ml of THF, and the reaction mixture is stirred at room temperature for 3 h. 262 ml (4.50 mol) of ethanol, 650 ml (2.6 mol) of aqueous sodium hydroxide solution (4 M) and 360 ml (4.11 mol) of aqueous hydrogen peroxide soln. (35%) are added successively to the batch, during which the internal temperature does not exceed 47° 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 (336 g of yellow oil) is purified by column chromatography (SiO2, dichloromethane: MTBE=8:2), giving 8-(4-ethoxy-2,3-difluorophenyl)-1,4-dioxaspiro[4.5]decan-7-ol as pale-yellow oil.

Workup

  1. addition(35%) are added successively to the batch, during which the internal temperature
  2. customdoes not exceed 47° 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 (336 g of yellow oil) is purified by column chromatography (SiO2, dichloromethane: MTBE=8:2)

Sources & evidence

ORD record
ord-c7643cc717c944e68a3922ccc90cf976
Source dataset
uspto-grants-2008_08
Patent number
US07417157B2

Reaction notes

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