Water → HCID 22165625, compound

HRID 70573Notes

Reaction equation

HRID 70573 reaction equation
[H-].[Na+].[CH3:3]I.[Br:5][C:6]1[CH:11]=[CH:10][C:9]([CH2:12][CH2:13][CH2:14][CH2:15][OH:16])=[CH:8][CH:7]=1.O>CN(C)C=O>[Br:5][C:6]1[CH:7]=[CH:8][C:9]([CH2:12][CH2:13][CH2:14][CH2:15][O:16][CH3:3])=[CH:10][CH:11]=1

Participants

6

Reactant 4

HCID 962WaterHCID 6328Methyl iodideHCID 24758Sodium hydrideHCID 282961564-(4-Bromophenyl)butan-1-ol

Product 1

HCID 22165625HCID 22165625, compoundYield 88%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

Sodium hydride (purity: 55%, 434 mg) and methyl iodide (0.62 mL) were added to a solution of 4-(4-bromophenyl)butan-1-ol obtained in Reference Example 5-21(1) in N,N-dimethylformamide (30 mL) under ice-cooling, and the mixture was stirred at room temperature for 7.5 hours. Water was added to the reaction solution, followed by extraction with a mixture of hexane-ethyl acetate (1:1). The organic layer was dried over sodium sulfate and filtered. The solvent was then evaporated under reduced pressure. The residue was purified by silica gel column chromatography (hexane:ethyl acetate=50:1→20:1→10:1) to give the title compound (1.06 g, 88%).

Workup

  1. temperaturecooling
  2. extractionfollowed by extraction with a mixture of hexane-ethyl acetate (1:1)
  3. dry with materialThe organic layer was dried over sodium sulfate
  4. filtrationfiltered
  5. customThe solvent was then evaporated under reduced pressure
  6. customThe residue was purified by silica gel column chromatography (hexane:ethyl acetate=50:1→20:1→10:1)

Sources & evidence

ORD record
ord-d7d330592b29492e9fc3bd3ebed49a6a
Source dataset
uspto-grants-2014_09
Patent number
US08822503B2

Reaction notes

Loading…