HCID 67944144, compound → HCID 15133053, compound

HRID 1086076Notes

Reaction equation

HRID 1086076 reaction equation
[Cr](Cl)([O-])(=O)=O.[NH+]1C=CC=CC=1.[F:12][C:13]1[CH:18]=[CH:17][C:16]([CH:19]([C:30]2[CH:35]=[CH:34][C:33]([F:36])=[CH:32][CH:31]=2)[C:20]([CH:23]([CH:27]([CH3:29])[CH3:28])[CH:24]([CH3:26])[CH3:25])=[CH:21][OH:22])=[CH:15][CH:14]=1>C(Cl)Cl>[F:12][C:13]1[CH:14]=[CH:15][C:16]([C:19]([C:30]2[CH:31]=[CH:32][C:33]([F:36])=[CH:34][CH:35]=2)=[C:20]([CH:23]([CH:24]([CH3:25])[CH3:26])[CH:27]([CH3:29])[CH3:28])[CH:21]=[O:22])=[CH:17][CH:18]=1

Participants

4

Reactant 2

HCID 67944144HCID 67944144, compoundHCID 178418287HCID 178418287, compound

Product 1

HCID 15133053HCID 15133053, compoundYield 95.7%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

Pyridinium chlorochromate (3.5 g) was added to a solution of 3,3-bis(4-fluorophenyl)-2-[2-methyl-1-(1-methylethyl)propyl]propenol (2.1 g, 6.1 mmol) in 75 mL of methylene chloride and the mixture stirred for 48 hours. The methylene chloride was decanted from the gummy precipitate which was washed with fresh solvent. The combined methylene chloride solutions were concentrated in vacuo to give a dark oil. The oil was triturated with 4×50 mL volumes of hexane. The hexane solutions were concentrated in vacuo to give 2.0 g of the title compound as a light yellow oil. M.S.(EI): m/e =342 for M+ of C22H24F2O.

Workup

  1. customThe methylene chloride was decanted from the gummy precipitate which
  2. washwas washed with fresh solvent
  3. concentrationThe combined methylene chloride solutions were concentrated in vacuo
  4. customto give a dark oil
  5. customThe oil was triturated with 4×50 mL volumes of hexane
  6. concentrationThe hexane solutions were concentrated in vacuo

Sources & evidence

ORD record
ord-f6a7a601a9d34c3a89fccdb01b071eed
Source dataset
uspto-grants-1991_04
Patent number
US05011947

Reaction notes

Loading…