Water → HCID 67396288, compound

HRID 70590Notes

Reaction equation

HRID 70590 reaction equation
[C:1](=O)([O-])[O-].[K+].[K+].CI.[Cl:9][C:10]1[CH:15]=[C:14](/[C:16](/[C:23]2[CH:28]=[CH:27][C:26]([CH2:29][CH3:30])=[C:25]([O:31][CH3:32])[N:24]=2)=[CH:17]\[CH:18]2[CH2:22][CH2:21][CH2:20][CH2:19]2)[CH:13]=[CH:12][C:11]=1[OH:33].O>CN(C)C=O>[Cl:9][C:10]1[CH:15]=[C:14](/[C:16](/[C:23]2[N:24]=[C:25]([O:31][CH3:32])[C:26]([CH2:29][CH3:30])=[CH:27][CH:28]=2)=[CH:17]\[CH:18]2[CH2:19][CH2:20][CH2:21][CH2:22]2)[CH:13]=[CH:12][C:11]=1[O:33][CH3:1]

Participants

6

Reactant 4

HCID 962WaterHCID 6328Methyl iodideHCID 11430Potassium CarbonateHCID 67397793HCID 67397793, compound

Product 1

HCID 67396288HCID 67396288, compoundYield 77.3%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

Potassium carbonate (188 mg) and methyl iodide (73 μL) were sequentially added to a solution of 2-chloro-4-[(E)-2-cyclopentyl-1-(5-ethyl-6-methoxypyridin-2-yl)ethenyl]phenol (163 mg) in N,N-dimethylformamide (3 mL), and the mixture was stirred at room temperature for four hours. The reaction solution was poured into water, followed by extraction with ethyl acetate. The organic layer was washed with brine, dried over anhydrous magnesium sulfate and filtered. The solvent was then evaporated under reduced pressure. The residue was purified by silica gel column chromatography (hexane:ethyl acetate=10:0→2:1) to give 6-[(E)-1-(3-chloro-4-methoxyphenyl)-2-cyclopentylethenyl]-3-ethyl-2-methoxypyridine as a yellow oil (131 mg, 77%).

Workup

  1. extractionfollowed by extraction with ethyl acetate
  2. washThe organic layer was washed with brine
  3. dry with materialdried over anhydrous magnesium 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=10:0→2:1)

Sources & evidence

ORD record
ord-767eea22549340b5a9025463524fa0da
Source dataset
uspto-grants-2014_09
Patent number
US08822503B2

Reaction notes

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