Hydrogen Peroxide → HCID 22293532, compound

HRID 966987Notes

Reaction equation

HRID 966987 reaction equation
B.[O:2]1[CH2:6][CH2:5]CC1.[C:7]1([C:13]2(/[CH:23]=[CH:24]/[CH2:25][C:26]3[CH:31]=[C:30]([C:32]([F:35])([F:34])[F:33])[CH:29]=[C:28]([C:36]([F:39])([F:38])[F:37])[CH:27]=3)[CH2:22][CH2:21][C:16]3([O:20][CH2:19][CH2:18][O:17]3)[CH2:15][CH2:14]2)[CH:12]=[CH:11][CH:10]=[CH:9][CH:8]=1.[OH-:40].[Na+].OO>O>[C:6]([O:2][CH:23]([C:13]1([C:7]2[CH:8]=[CH:9][CH:10]=[CH:11][CH:12]=2)[CH2:22][CH2:21][C:16]2([O:20][CH2:19][CH2:18][O:17]2)[CH2:15][CH2:14]1)[CH2:24][CH2:25][C:26]1[CH:31]=[C:30]([C:32]([F:33])([F:34])[F:35])[CH:29]=[C:28]([C:36]([F:39])([F:38])[F:37])[CH:27]=1)(=[O:40])[CH3:5]

Participants

6

Reactant 4

HCID 784Hydrogen PeroxideHCID 14798Sodium HydroxideHCID 2723981Borane;tetrahydrofuranHCID 22293462HCID 22293462, compound

Product 1

HCID 22293532HCID 22293532, compound

Reagents, catalysts & solvents 1

HCID 962WaterSolvent2×

Procedure

Borane-tetrahydrofuran complex (1.0M in tetrahydrofuran, 12 mL, 12 mmol) was added over 10 minutes to a solution of (E)-8-phenyl-8-{3-[3,5-bis(trifluoromethyl)phenyl]prop-1-enyl}1,4-dioxaspiro[4.5]decane (Description 35, 1.88 g, 4 mmol) and the mixture was stirred at room temperature for 4.5 hours. Water (2 mL) then aqueous sodium hydroxide (4M, 20 mL) and aqueous hydrogen peroxide (30 w/v %, 20 mL) were added and the mixture was stirred at room temperature for 30 minutes. Water (150 mL) was added and the mixture was extracted with ether (2×150 mL). The combined organic fractions were dried (MgSO4) and the solvent was evaporated under reduced pressure. The residue was dissolved in pyridine (10 mL) and 4-dimethylaminopyridine (10 mg) and acetic anhydride (5 mL) were added. The mixture was stirred at room temperature for 4 hours, then water (150 mL) was added. The mixture was extracted with ethyl acetate (2×150 mL) and the combined organic fractions were washed with water (2×150 mL) and aqueous copper sulfate (5%, 2×100 mL), dried (MgSO4) and the solvent was evaporated under reduced pressure. The residue was purified by flash column chromatography on silica gel, eluting with CH2Cl2/EtOAc (99:1 increasing to 95:5), to give:

Workup

  1. stirringthe mixture was stirred at room temperature for 30 minutes
  2. extractionthe mixture was extracted with ether (2×150 mL)
  3. dry with materialThe combined organic fractions were dried (MgSO4)
  4. customthe solvent was evaporated under reduced pressure
  5. dissolutionThe residue was dissolved in pyridine (10 mL)
  6. addition4-dimethylaminopyridine (10 mg) and acetic anhydride (5 mL) were added
  7. stirringThe mixture was stirred at room temperature for 4 hours
  8. additionwater (150 mL) was added
  9. extractionThe mixture was extracted with ethyl acetate (2×150 mL)
  10. washthe combined organic fractions were washed with water (2×150 mL) and aqueous copper sulfate (5%, 2×100 mL)
  11. dry with materialdried (MgSO4)
  12. customthe solvent was evaporated under reduced pressure
  13. customThe residue was purified by flash column chromatography on silica gel
  14. washeluting with CH2Cl2/EtOAc (99:1 increasing to 95:5)
  15. customto give

Sources & evidence

ORD record
ord-d61fe6c8e62d43a4a4226f4cfe7f5b31
Source dataset
uspto-grants-2005_10
Patent number
US06953792B2

Reaction notes

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