Hydrochloric Acid → HCID 20794696, compound

HRID 1485060Notes

Reaction equation

HRID 1485060 reaction equation
[H-].[Na+].[F:3][C:4]([F:8])([F:7])[CH2:5][OH:6].[F:9][C:10]1[CH:11]=[C:12]([CH:15]=[CH:16][C:17]=1F)[CH:13]=[O:14].Cl>CN(C)C=O>[F:9][C:10]1[CH:11]=[C:12]([CH:15]=[CH:16][C:17]=1[O:6][CH2:5][C:4]([F:8])([F:7])[F:3])[CH:13]=[O:14]

Participants

6

Reactant 4

HCID 313Hydrochloric AcidHCID 64092,2,2-TrifluoroethanolHCID 24758Sodium hydrideHCID 5880883,4-Difluorobenzaldehyde

Product 1

HCID 20794696HCID 20794696, compoundYield 80%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

To a suspension of sodium hydride (60% dispersion in mineral oil, 0.844 g) in N,N-dimethylfounamide (30.0 mL), 2,2,2-trifluoroethanol (2.11 g) was added at 0° C. and thereafter the mixture was stirred at room temperature for 30 minutes. To the reaction mixture, a solution of 3,4-difluorobenzaldehyde (2.00 g) in N,N-dimethylformamide (10.0 mL) was added and thereafter the mixture was stirred at room temperature for 30 minutes. After adding 1 mol/L hydrochloric acid at 0° C., three extractions were conducted with ethyl acetate. The combined organic layers were passed through a phase separator and thereafter concentrated under reduced pressure. The resulting residue was purified by silica gel column chromatography (n-hexane:ethyl acetate=80:20-30:70) to give the titled compound as a colorless oil (2.50 g).

Workup

  1. additionwas added at 0° C.
  2. stirringthe mixture was stirred at room temperature for 30 minutes
  3. extractionthree extractions
  4. concentrationconcentrated under reduced pressure
  5. customThe resulting residue was purified by silica gel column chromatography (n-hexane:ethyl acetate=80:20-30:70)

Sources & evidence

ORD record
ord-4bde3bc648c24cb29ebd146f210442cd
Source dataset
uspto-grants-2016_08
Patent number
US09422240B2

Reaction notes

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