Hydrochloric Acid → 5,5,5-Trifluoro-2-[6-(4-trifluoromethyl-phenyl)-pyridin-3-yl]-pentanal

HRID 1669306Notes

Reaction equation

HRID 1669306 reaction equation
[F:1][C:2]([F:26])([F:25])[CH2:3][CH2:4][C:5]([C:9]1[CH:10]=[CH:11][C:12]([C:15]2[CH:20]=[CH:19][C:18]([C:21]([F:24])([F:23])[F:22])=[CH:17][CH:16]=2)=[N:13][CH:14]=1)=[CH:6][O:7]C.O1CCCC1.Cl.[OH-].[Na+]>C(OCC)C>[F:26][C:2]([F:1])([F:25])[CH2:3][CH2:4][CH:5]([C:9]1[CH:14]=[N:13][C:12]([C:15]2[CH:20]=[CH:19][C:18]([C:21]([F:22])([F:23])[F:24])=[CH:17][CH:16]=2)=[CH:11][CH:10]=1)[CH:6]=[O:7]

Participants

6

Reactant 4

HCID 313Hydrochloric AcidHCID 8028TetrahydrofuranHCID 14798Sodium HydroxideHCID 866203565-(4,4,4-Trifluoro-1-methoxymethylene-butyl)-2-(4-trifluoromethyl-phenyl)-pyridine

Product 1

HCID 866203575,5,5-Trifluoro-2-[6-(4-trifluoromethyl-phenyl)-pyridin-3-yl]-pentanalYield 91.7%

Reagents, catalysts & solvents 1

HCID 3283Diethyl EtherSolvent

Procedure

A solution of 5-(4,4,4-trifluoro-1-methoxymethylene-butyl)-2-(4-trifluoromethyl-phenyl)-pyridine (4.1 g, 10.9 mmol) and tetrahydrofuran (50 mL) is treated with concentrated hydrochloric acid (5 mL) and heated to reflux under nitrogen. The reaction is monitored by HPLC and allowed to cool upon completion. The solution is neutralized with 20% NaOH solution and diluted with diethyl ether. The two phases are separated and the organic layer washed with brine and water. The organic layer is dried over anhydrous sodium sulfate, filtered, and concentrated. Chromatography gives purified 5,5,5-trifluoro-2-[6-(4-trifluoromethyl-phenyl)-pyridin-3-yl]-pentanal (3.6 g, 10 mmol) 79% yield.

Workup

  1. temperatureheated
  2. temperatureto reflux under nitrogen
  3. temperatureto cool upon completion
  4. customThe two phases are separated
  5. washthe organic layer washed with brine and water
  6. dry with materialThe organic layer is dried over anhydrous sodium sulfate
  7. filtrationfiltered
  8. concentrationconcentrated
  9. customChromatography gives

Sources & evidence

ORD record
ord-59c285660d7e4f79acbc03d30a922e5b
Source dataset
uspto-grants-2011_08
Patent number
US07989457B2

Reaction notes

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