Methyl iodide → HCID 23136312, compound

HRID 1678606Notes

Reaction equation

HRID 1678606 reaction equation
[F:1][C:2]1[CH:3]=[C:4]([CH2:24][CH2:25][C:26]([O:28][CH2:29][CH3:30])=[O:27])[CH:5]=[CH:6][C:7]=1[O:8][CH2:9][C:10]1[CH:15]=[C:14]([O:16][C:17]2[CH:22]=[CH:21][CH:20]=[CH:19][CH:18]=2)[CH:13]=[C:12]([OH:23])[CH:11]=1.CI.[C:33](=O)([O-])[O-].[K+].[K+]>CC(C)=O.C(OCC)(=O)C>[F:1][C:2]1[CH:3]=[C:4]([CH2:24][CH2:25][C:26]([O:28][CH2:29][CH3:30])=[O:27])[CH:5]=[CH:6][C:7]=1[O:8][CH2:9][C:10]1[CH:15]=[C:14]([O:16][C:17]2[CH:22]=[CH:21][CH:20]=[CH:19][CH:18]=2)[CH:13]=[C:12]([O:23][CH3:33])[CH:11]=1

Participants

6

Reactant 3

HCID 6328Methyl iodideHCID 11430Potassium CarbonateHCID 23136481HCID 23136481, compound

Product 1

HCID 23136312HCID 23136312, compoundYield 100%

Reagents, catalysts & solvents 2

HCID 180AcetoneSolventHCID 8857Ethyl AcetateSolvent

Procedure

To a solution of ethyl 3-{3-fluoro-4-[(3-hydroxy-5-phenoxybenzyl)oxy]phenyl}propanoate (0.30 g, 0.73 mmol) and methyl iodide (2.2 mL, 14.6 mmol) in acetone (10 mL) was added potassium carbonate (0.52 g, 3.76 mmol), and the mixture was heated under reflux and stirred for 4 hours. The reaction solution was diluted with ethyl acetate, filtered, washed with water, and then concentrated under reduced pressure. The resulting residue was purified with silica gel column chromatography (hexane/ethyl acetate=7:3) to give the title compound (0.31 g, yield 99%) as an oily matter.

Workup

  1. temperaturethe mixture was heated
  2. temperatureunder reflux
  3. filtrationfiltered
  4. washwashed with water
  5. concentrationconcentrated under reduced pressure
  6. customThe resulting residue was purified with silica gel column chromatography (hexane/ethyl acetate=7:3)

Sources & evidence

ORD record
ord-ae6424b350f848f7a0602b0496f8c1b7
Source dataset
uspto-grants-2011_08
Patent number
US08008525B2

Reaction notes

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