HCID 20059356, compound → HCID 15133054, compound

HRID 1086081Notes

Reaction equation

HRID 1086081 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:27]2[CH:32]=[CH:31][C:30]([F:33])=[CH:29][CH:28]=2)[CH:20]([C:23]([CH3:26])([CH3:25])[CH3:24])[CH2:21][OH:22])=[CH:15][CH:14]=1>C(Cl)Cl>[F:12][C:13]1[CH:14]=[CH:15][C:16]([C:19]([C:27]2[CH:28]=[CH:29][C:30]([F:33])=[CH:31][CH:32]=2)=[C:20]([C:23]([CH3:26])([CH3:25])[CH3:24])[CH:21]=[O:22])=[CH:17][CH:18]=1

Participants

4

Reactant 2

HCID 20059356HCID 20059356, compoundHCID 178418287HCID 178418287, compound

Product 1

HCID 15133054HCID 15133054, compoundYield 42.1%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Conditions

Temperature
25 °C

Procedure

A mixture of pyridinium chlorochromate (3.8 g) and 3,3-bis-(4-fluorophenyl)-2-(1,1-dimethylethyl)propanol (2.4 g, 7.9 mmol) in 100 mL of methylene chloride was stirred at 25° C. for 64 hours during which time a gummy precipitate separated. The solvent was decanted from the precipitate and the residue rinsed with two 50 mL portions of methylene chloride. The combined methylene chloride solution was concentrated in vacuo. The residue was trituated with three 60 mL portions of hexane. The hexane solution was concentrated in vacuo and the residue crystallized from fresh hexane to give 1.0 g of the title compound; m.p. =49°-51° C. MS(CI): m/e =300 for M+.

Workup

  1. customseparated
  2. customThe solvent was decanted from the precipitate
  3. washthe residue rinsed with two 50 mL portions of methylene chloride
  4. concentrationThe combined methylene chloride solution was concentrated in vacuo
  5. concentrationThe hexane solution was concentrated in vacuo
  6. customthe residue crystallized from fresh hexane

Sources & evidence

ORD record
ord-315bc1a705764dd88b4d7bee2a7e135d
Source dataset
uspto-grants-1991_04
Patent number
US05011947

Reaction notes

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