HCID 86639434, compound → HCID 86639433, compound

HRID 1690218Notes

Reaction equation

HRID 1690218 reaction equation
[F:1][C:2]([F:33])([F:32])[C:3]([C:12]1[CH:28]=[CH:27][C:15]([O:16][C:17]2[CH:18]=[CH:19][C:20]([CH2:24][CH2:25][OH:26])=[N+:21]([O-])[CH:22]=2)=[C:14]([CH2:29][CH2:30][CH3:31])[CH:13]=1)([O:8][CH2:9][O:10][CH3:11])[C:4]([F:7])([F:6])[F:5]>C(O)(=O)C.[Zn]>[F:33][C:2]([F:1])([F:32])[C:3]([C:12]1[CH:28]=[CH:27][C:15]([O:16][C:17]2[CH:18]=[CH:19][C:20]([CH2:24][CH2:25][OH:26])=[N:21][CH:22]=2)=[C:14]([CH2:29][CH2:30][CH3:31])[CH:13]=1)([O:8][CH2:9][O:10][CH3:11])[C:4]([F:7])([F:6])[F:5]

Participants

4

Reactant 1

HCID 86639434HCID 86639434, compound

Product 1

HCID 86639433HCID 86639433, compoundYield 90.3%

Reagents, catalysts & solvents 2

HCID 23994ZincCatalystHCID 176Acetic AcidSolvent

Procedure

To a solution of 5-(4-(1,1,1,3,3,3-hexafluoro-2-(methoxymethoxy)propan-2-yl)-2-propylphenoxy)-2-(2-hydroxyethyl)pyridine 1-oxide (2.29 g, 4.74 mmol) in acetic acid (24 mL), zinc powder (6.2 g, 94.7 mmol) was added, and the resultant mixture was stirred at room temperature for 4 hours. After completion of the reaction, the reaction solution was filtered using celite, added with a saturated aqueous solution of sodium hydrogen carbonate, and extracted with ethyl acetate. The organic layer was washed with brine and dried using sodium sulfate. After filtration, the filtrate was concentrated in vacuo. The obtained residue was purified using silica-gel column chromatography (hexane/acetone) and 2-(5-(4-(1,1,1,3,3,3-hexafluoro-2-(methoxymethoxy)propan-2-yl)-2-propylphenoxy)pyridin-2-yl)ethanol (2.0 g, yield 90%) was obtained as a yellow oil.

Workup

  1. customAfter completion of the reaction
  2. filtrationthe reaction solution was filtered
  3. additionadded with a saturated aqueous solution of sodium hydrogen carbonate
  4. extractionextracted with ethyl acetate
  5. washThe organic layer was washed with brine
  6. customdried
  7. filtrationAfter filtration
  8. concentrationthe filtrate was concentrated in vacuo
  9. customThe obtained residue was purified

Sources & evidence

ORD record
ord-1e90afb7ba4640a3b54bcda897c4b1c8
Source dataset
uspto-grants-2012_04
Patent number
US08153634B2

Reaction notes

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