1-Propanol → HCID 59820902, compound

HRID 1363661Notes

Reaction equation

HRID 1363661 reaction equation
[CH2:1]([OH:4])[CH2:2][CH3:3].[H-].[Na+].Cl[C:8]1[CH:13]=[CH:12][C:11]([N+:14]([O-:16])=[O:15])=[CH:10][C:9]=1[C:17]1[CH:22]=[CH:21][C:20]([O:23][C:24]([F:27])([F:26])[F:25])=[CH:19][CH:18]=1>CN(C)C=O.O>[N+:14]([C:11]1[CH:12]=[CH:13][C:8]([O:4][CH2:1][CH2:2][CH3:3])=[C:9]([C:17]2[CH:22]=[CH:21][C:20]([O:23][C:24]([F:27])([F:26])[F:25])=[CH:19][CH:18]=2)[CH:10]=1)([O-:16])=[O:15]

Participants

6

Reactant 3

HCID 10311-PropanolHCID 24758Sodium hydrideHCID 59820859HCID 59820859, compound

Product 1

HCID 59820902HCID 59820902, compoundYield 54.5%

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 6228DimethylformamideSolvent2×

Procedure

1-Propanol (284 mg, 4.72 mmol) was added dropwise at a slow speed to a suspension of sodium hydride (206 mg, 4.72 mmol) in dimethylformamide (4 ml) at 0° under argon atmosphere, then the mixture was stirred at room temperature for 30 minutes. A solution of 2-chloro-5-nitro-4′-(trifluoromethoxy)biphenyl (1.00 g, 3.15 mmol) in dimethylformamide (2 ml) was added dropwise at a slow speed to this mixture at OD, and then stirred at room temperature for 2 hours. The reaction mixture was diluted with water and extracted with ethyl acetate. The organic layer was washed with saturated brine, and dried over anhydrous sodium sulfate. The residue obtained by evaporation of the solvent under reduced pressure was purified by column chromatography on silica gel (n-hexane:ethyl acetate=6:1) to give the title compound (586g, 54.5%) as a pale yellow solid.

Workup

  1. stirringstirred at room temperature for 2 hours
  2. extractionextracted with ethyl acetate
  3. washThe organic layer was washed with saturated brine
  4. dry with materialdried over anhydrous sodium sulfate
  5. customThe residue obtained by evaporation of the solvent under reduced pressure
  6. customwas purified by column chromatography on silica gel (n-hexane:ethyl acetate=6:1)

Sources & evidence

ORD record
ord-dfbc0e9078bc4e8a81a844aeba23212d
Source dataset
uspto-grants-2011_02
Patent number
US07884234B2

Reaction notes

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