Hydrogen Peroxide → HCID 57565075, compound

HRID 1726866Notes

Reaction equation

HRID 1726866 reaction equation
[F:1][C:2]([F:30])([F:29])[C:3]1[CH:4]=[C:5]([CH:22]=[C:23]([C:25]([F:28])([F:27])[F:26])[CH:24]=1)[CH2:6][O:7][CH2:8][C:9]1([C:16]2[CH:21]=[CH:20][CH:19]=[CH:18][CH:17]=2)[CH2:15][CH2:14][CH:13]=[CH:12][CH2:11][CH2:10]1.[OH2:31].OO.[OH-].[Na+]>C1COCC1.C(OCC)(=O)C>[F:1][C:2]([F:29])([F:30])[C:3]1[CH:4]=[C:5]([CH:22]=[C:23]([C:25]([F:28])([F:27])[F:26])[CH:24]=1)[CH2:6][O:7][CH2:8][C:9]1([C:16]2[CH:21]=[CH:20][CH:19]=[CH:18][CH:17]=2)[CH2:15][CH2:14][CH2:13][CH:12]([OH:31])[CH2:11][CH2:10]1

Participants

7

Reactant 4

HCID 784Hydrogen PeroxideHCID 962WaterHCID 14798Sodium HydroxideHCID 57565083HCID 57565083, compound

Product 1

HCID 57565075HCID 57565075, compound

Reagents, catalysts & solvents 2

HCID 8028TetrahydrofuranSolventHCID 8857Ethyl AcetateSolvent

Procedure

To a solution of (Z)-5-((3,5-bis(trifluoromethyl)benzyloxy)methyl)-5-phenylcyclohept-1-ene (56 mg) from step E in THF (0.55 mL) at 0° C. was added borane-tetrahydrofuran complex (1.5 M solution, 0.17 mL) drop wise, 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 (10.50 mL) was added slowly followed by 30% hydrogen peroxide (0.19 mL) and 1 N sodium hydroxide (0.30 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 (27 mg). 1H NMR (400 MHz, CDCl3) δ 1.3-2.4 (m), 3.40 (s), 3.44 (s), 4.43 (s), 7.32 (m), 7.56 (s), and 7.73 (s). HRMS m/z calcd for C23H23F6O2 (M−H)− 445.1602, found 445.1607.

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-41bf61ec97b84dd4a8deb3fd9ec19655
Source dataset
uspto-grants-2009_02
Patent number
US07494986B2

Reaction notes

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