Oxygen → HCID 86630498, compound

HRID 1869776Notes

Reaction equation

HRID 1869776 reaction equation
[F:1][C:2]([S:35]([C:38]1[CH:43]=[CH:42][CH:41]=[CH:40][CH:39]=1)(=[O:37])=[O:36])([S:26]([C:29]1[CH:34]=[CH:33][CH:32]=[CH:31][CH:30]=1)(=[O:28])=[O:27])[CH:3]([C:16]1[CH:21]=[CH:20][C:19]([CH2:22][CH:23]([CH3:25])[CH3:24])=[CH:18][CH:17]=1)/[CH:4]=C/C1C=CC(CC(C)C)=CC=1.[O:44]=[O+][O-].O=O.[BH4-].[Na+].[Cl-].[NH4+]>CO.C(Cl)Cl>[F:1][C:2]([S:35]([C:38]1[CH:43]=[CH:42][CH:41]=[CH:40][CH:39]=1)(=[O:37])=[O:36])([S:26]([C:29]1[CH:34]=[CH:33][CH:32]=[CH:31][CH:30]=1)(=[O:28])=[O:27])[CH:3]([C:16]1[CH:21]=[CH:20][C:19]([CH2:22][CH:23]([CH3:25])[CH3:24])=[CH:18][CH:17]=1)[CH2:4][OH:44]

Participants

8

Reactant 5

HCID 977OxygenHCID 24823Ozone2×HCID 25517Ammonium ChlorideHCID 4311764Sodium borohydrideHCID 86630499HCID 86630499, compound

Product 1

HCID 86630498HCID 86630498, compoundYield 98%

Reagents, catalysts & solvents 2

HCID 887MethanolSolventHCID 6344DichloromethaneSolvent

Procedure

A solution of (E)-4-fluoro-1,3-bis(4-isobutylphenyl)-4,4-bis(phenylsulfonyl) but-1-ene (5a, 506 mg, 0.818 mmol, 1.0 eq) in 20 mL of MeOH and 7 mL of CH2Cl2 was cooled to −78° C. Ozone gas generated by an ozone generator was introduced to this solution for 30 minutes, and then O2 was introduced for 5 minutes to remove excess ozone. Next, the solution was charged with NaBH4 (93.1 mg, 2.49 mmol, 3.0 eq), and the temperature was increased over two hours to room temperature. The reactant solution was then charged with saturated aqueous ammonium chloride solution. The aqueous layer was extracted with methylene chloride and then the extract was dried with anhydrous sodium sulfate. The solvent was removed under reduced pressure by distillation, and then the reactant was purified by column chromatography (hexane:ethyl acetate=6:4) to obtain 3-fluoro-2-(4-isobutylphenyl)-3,3-bis(phenylsulfonyl)propan-1-ol as a white solid (393 mg, 98%).

Workup

  1. additionwas introduced to this solution for 30 minutes
  2. customto remove excess ozone
  3. temperaturethe temperature was increased over two hours to room temperature
  4. extractionThe aqueous layer was extracted with methylene chloride
  5. dry with materialthe extract was dried with anhydrous sodium sulfate
  6. customThe solvent was removed under reduced pressure by distillation
  7. customthe reactant was purified by column chromatography (hexane:ethyl acetate=6:4)

Sources & evidence

ORD record
ord-e73f1b30faa04ed3905eb7cf974d83fa
Source dataset
uspto-grants-2009_12
Patent number
US07638654B2

Reaction notes

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