Sodium Hydroxide → HCID 22250820, compound

HRID 890474Notes

Reaction equation

HRID 890474 reaction equation
C([O:3][C:4](=O)[C:5]1[C:10]([C:11]([F:14])([F:13])[F:12])=[CH:9][C:8]([C:15]2[CH:20]=[CH:19][C:18]([C:21]([F:24])([F:23])[F:22])=[CH:17][CH:16]=2)=[N:7][C:6]=1[CH3:25])C.[H-].[Al+3].[Li+].[H-].[H-].[H-].[OH-].[Na+]>C(OCC)C>[CH3:25][C:6]1[C:5]([CH2:4][OH:3])=[C:10]([C:11]([F:13])([F:14])[F:12])[CH:9]=[C:8]([C:15]2[CH:20]=[CH:19][C:18]([C:21]([F:23])([F:22])[F:24])=[CH:17][CH:16]=2)[N:7]=1

Participants

5

Reactant 3

HCID 14798Sodium HydroxideHCID 21226445Aluminium lithium hydrideHCID 86597779851070-23-0

Product 1

HCID 22250820HCID 22250820, compoundYield 48%

Reagents, catalysts & solvents 1

HCID 3283Diethyl EtherSolvent2×

Conditions

Temperature
0 °C

Procedure

A solution of 2-methyl-4-trifluoromethyl-6-(4-trifluoromethyl-phenyl)-nicotinic acid ethyl ester (200 mg, 0.5 mmol) in diethyl ether (3 ml) was added to a suspension of lithium aluminium hydride (40 mg, 1 mmol) in diethyl ether (6 ml) under an argon atmosphere at ambient temperature within 5 min. The mixture was stirred at reflux for 12 h, cooled to 0° C. and treated cautiously with ice water (6 ml) and 10% aqueous NaOH (3 ml). The reaction mixture was filtered over celite, t-butyl methylether was added and the layers were separated. The aqueous layer was extracted one more time with t-butyl methylether, the combined organic layers were washed with ice water/brine 1/1 and dried over sodium sulfate. Removal of the solvent under reduced pressure gave a brown oil which was purified by column chromatography (silica gel, heptane/AcOEt) to yield 80 mg (240 μmol, 45%) of the title compound as yellow crystals.

Workup

  1. temperatureat reflux for 12 h
  2. filtrationThe reaction mixture was filtered over celite, t-butyl methylether
  3. additionwas added
  4. customthe layers were separated
  5. extractionThe aqueous layer was extracted one more time with t-butyl methylether
  6. washthe combined organic layers were washed with ice water/brine 1/1
  7. dry with materialdried over sodium sulfate
  8. customRemoval of the solvent under reduced pressure
  9. customgave a brown oil which
  10. customwas purified by column chromatography (silica gel, heptane/AcOEt)

Sources & evidence

ORD record
ord-2eb29755016248699a9faa015c4674c5
Source dataset
uspto-grants-2006_02
Patent number
US06995263B2

Reaction notes

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