Water → HCID 86639429, compound

HRID 1690210Notes

Reaction equation

HRID 1690210 reaction equation
[CH2:1]([O:8][C:9]1[CH:10]=[CH:11][C:12]([C:18]([OH:27])([C:23]([F:26])([F:25])[F:24])[C:19]([F:22])([F:21])[F:20])=[N:13][C:14]=1[CH2:15][CH2:16][CH3:17])[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.[H-].[Na+].[Cl-].[CH3:31][O:32][CH2:33]OCOC.O>CN(C=O)C>[CH2:1]([O:8][C:9]1[C:14]([CH2:15][CH2:16][CH3:17])=[N:13][C:12]([C:18]([O:27][CH2:31][O:32][CH3:33])([C:23]([F:26])([F:25])[F:24])[C:19]([F:22])([F:20])[F:21])=[CH:11][CH:10]=1)[C:2]1[CH:3]=[CH:4][CH:5]=[CH:6][CH:7]=1

Participants

6

Reactant 4

HCID 962WaterHCID 24758Sodium hydrideHCID 87198314HCID 87198314, compoundHCID 131729613HCID 131729613, compound

Product 1

HCID 86639429HCID 86639429, compoundYield 68%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

2-(5-(Benzyloxy)-6-propylpyridin-2-yl)-1,1,1,3,3,3-hexafluoropropan-2-ol (537 mg, 1.37 mmol) was dissolved in N,N′-dimethylformamide (2.5 mL) and added with sodium hydride (purity 50%) (79 mg, 1.64 mmol) and methoxymethyl ether chloride (113 μL, 1.50 mmol) under ice-cold conditions The resultant mixture was stirred under ice-cold conditions for 1.5 hours and then further stirred at room temperature for 45 minutes. After completion of the reaction, the reaction solution was added with water and extracted with ethyl acetate. The organic layer was washed with brine, dried using anhydrous sodium sulfate, and concentrated in vacuo. The obtained residue was purified using silica-gel column chromatography (hexane/ethyl acetate), and 3-(benzyloxy)-6-(1,1,1,3,3,3-hexafluoro-2-(methoxymethoxy)propan-2-yl)-2-propylpyridine (407 mg, yield 68%) was obtained as a colorless oil.

Workup

  1. stirringfurther stirred at room temperature for 45 minutes
  2. customAfter completion of the reaction
  3. extractionextracted with ethyl acetate
  4. washThe organic layer was washed with brine
  5. customdried
  6. concentrationconcentrated in vacuo
  7. customThe obtained residue was purified

Sources & evidence

ORD record
ord-b013c50a5507487e88eade130384054b
Source dataset
uspto-grants-2012_04
Patent number
US08153634B2

Reaction notes

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