Toluene → HCID 86591099, compound

HRID 916010Notes

Reaction equation

HRID 916010 reaction equation
[Cl:1][C:2]1[C:3]([F:32])=[C:4]([CH:25]=[C:26]([C:28]([F:31])([F:30])[F:29])[CH:27]=1)[CH2:5][C:6]([OH:24])([CH2:11][C:12](C1C2OCCC=2C=CC=1)([CH3:14])[CH3:13])[C:7]([F:10])([F:9])[F:8].Cl[C:34]1[C:35](=[O:46])[C:36]([C:44]#N)=[C:37](C#N)[C:38](=O)[C:39]=1Cl.[C:47]1(C)C=CC=CC=1>CCOC(C)=O.[OH-].[Na+]>[O:46]1[C:35]2=[C:34]([CH:11]([CH:12]([CH3:13])[CH3:14])[C:6]([CH2:5][C:4]3[CH:25]=[C:26]([C:28]([F:29])([F:31])[F:30])[CH:27]=[C:2]([Cl:1])[C:3]=3[F:32])([OH:24])[C:7]([F:8])([F:10])[F:9])[CH:47]=[CH:44][C:36]2=[CH:37][CH:38]=[CH:39]1

Participants

6

Reactant 3

HCID 1140TolueneHCID 67752,3-Dichloro-5,6-dicyano-1,4-benzoquinoneHCID 10195692HCID 10195692, compound

Product 1

HCID 86591099HCID 86591099, compoundYield 50%

Reagents, catalysts & solvents 2

HCID 8857Ethyl AcetateSolventHCID 14798Sodium HydroxideSolvent

Procedure

A mixture of 20.0 mg (0.041 mmol) of 2-(3-chloro-2-fluoro-5-trifluoromethylbenzyl)-4-(2,3-dihydrobenzofuran-7-yl)-1,1,1-trifluoro-4-methylpentan-2-ol and 42.0 mg (0.185 mmol) of 2,3-dichloro-5,6-dicyano-1,4-benzoquinone (DDQ) in 4 mL of toluene was warmed at reflux for 18 hours. The solvent was lost overnight and the oil bath temperature was 145° C. The residue was diluted with 10 mL of EtOAc and 1 N aqueous sodium hydroxide, treated with decolorizing carbon, and filtered through diatomaceous earth. The basic aqueous was separated and extracted with two 5 mL portions of ethyl acetate. The combined organic layers were washed with two 5 mL portions of brine, three 5 mL portions of saturated aqueous ammonium chloride, two 5 mL portions of brine, dried over magnesium sulfate, filtered, and concentrated in vacuo to afford the crude product which was purified by preparative TLC (2 mm, EtOAc-hexanes (1:9), silica gel) to afford 9.9 mg (50%) of the title compound as an oil.

Workup

  1. temperaturewas warmed
  2. temperatureat reflux for 18 hours
  3. customwas 145° C
  4. additiontreated with decolorizing carbon
  5. filtrationfiltered through diatomaceous earth
  6. customThe basic aqueous was separated
  7. extractionextracted with two 5 mL portions of ethyl acetate
  8. washThe combined organic layers were washed with two 5 mL portions of brine, three 5 mL portions of saturated aqueous ammonium chloride, two 5 mL portions of brine
  9. dry with materialdried over magnesium sulfate
  10. filtrationfiltered
  11. concentrationconcentrated in vacuo
  12. customto afford the crude product which
  13. customwas purified by preparative TLC (2 mm, EtOAc-hexanes (1:9), silica gel)

Sources & evidence

ORD record
ord-6f663beac25d41c1907352a13a7ac52a
Source dataset
uspto-grants-2007_09
Patent number
US07268152B2

Reaction notes

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