Hydrogen Peroxide → HCID 58592523, compound

HRID 1178845Notes

Reaction equation

HRID 1178845 reaction equation
[C:1]1([C:7]2([CH2:12][O:13][CH2:14][C:15]3[CH:20]=[C:19]([C:21]([F:24])([F:23])[F:22])[CH:18]=[C:17]([C:25]([F:28])([F:27])[F:26])[CH:16]=3)[CH2:11][CH:10]=[CH:9][CH2:8]2)[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=1.[OH2:29].OO.[OH-].[Na+]>C1COCC1.C(OCC)(=O)C>[F:28][C:25]([F:26])([F:27])[C:17]1[CH:16]=[C:15]([CH:20]=[C:19]([C:21]([F:22])([F:23])[F:24])[CH:18]=1)[CH2:14][O:13][CH2:12][C:7]1([C:1]2[CH:2]=[CH:3][CH:4]=[CH:5][CH:6]=2)[CH2:11][CH2:10][CH:9]([OH:29])[CH2:8]1

Participants

7

Reactant 4

HCID 784Hydrogen PeroxideHCID 962WaterHCID 14798Sodium HydroxideHCID 58592538HCID 58592538, compound

Product 1

HCID 58592523HCID 58592523, compound

Reagents, catalysts & solvents 2

HCID 8028TetrahydrofuranSolventHCID 8857Ethyl AcetateSolvent

Procedure

To a solution of 1-(((1-phenylcyclopent-3-enyl)methoxy)methyl)-3,5-bis(trifluoromethyl)benzene (200 mg) in THF (0.55 mL) at 0° C. was added borane-tetrahydrofuran complex (1.0 M solution, 0.55 mL) dropwise, and the resulting solution was warmed to room temperature and stirred at room temperature for 12 h. The reaction mixture was cooled to 0° C., and water (1.0 mL) was added slowly followed by 30% hydrogen peroxide (0.19 mL) and 1 N sodium hydroxide (0.55 mL). The resulting solution was stirred at room temperature for 5 min, and ethyl acetate (2.0 mL) was added. The aqueous layer was extracted with ethyl acetate, the combined organic layers were dried over anhydrous sodium sulfate and filtered, and the filtrate was evaporated in vacuo. The residue was purified by preparative TLC eluting with 40% ethyl acetate/60% hexanes to give the title compound as an oily material. 1H NMR (400 MHz, CDCl3) δ 2.06 (m), 1.9-2.6 (m), 3.42 (s), 3.57 (q, J=8.8 Hz), 4.45 (s), 4.3-4.6 (m), 7.1-7.5 (m), 7.47 (s), 7.64 (s), 7.74 (s), and 7.76 (s).

Workup

  1. temperatureThe reaction mixture was cooled to 0° C.
  2. stirringThe resulting solution was stirred at room temperature for 5 min
  3. extractionThe aqueous layer was extracted with ethyl acetate
  4. dry with materialthe combined organic layers were dried over anhydrous sodium sulfate
  5. filtrationfiltered
  6. customthe filtrate was evaporated in vacuo
  7. customThe residue was purified by preparative TLC
  8. washeluting with 40% ethyl acetate/60% hexanes

Sources & evidence

ORD record
ord-0d2f51565a9f4e50b48bfcf56792701c
Source dataset
uspto-grants-2007_10
Patent number
US07276631B2

Reaction notes

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