Methyl iodide → HCID 66683883, compound

HRID 336089Notes

Reaction equation

HRID 336089 reaction equation
[O:1]1[C:5]2[CH:6]=[CH:7][CH:8]=[CH:9][C:4]=2[CH:3]=[C:2]1[CH:10](O)[CH:11]1[C:15](=[O:16])[C:14]([C:17]2[C:22]([CH3:23])=[CH:21][C:20]([CH3:24])=[CH:19][C:18]=2[CH3:25])=[C:13]([O:26][CH3:27])[CH2:12]1.C(=O)([O-])[O-].[K+].[K+].CI>CO>[O:1]1[C:5]2[CH:6]=[CH:7][CH:8]=[CH:9][C:4]=2[CH:3]=[C:2]1/[CH:10]=[C:11]1\[CH2:12][C:13]([O:26][CH3:27])=[C:14]([C:17]2[C:18]([CH3:25])=[CH:19][C:20]([CH3:24])=[CH:21][C:22]=2[CH3:23])[C:15]\1=[O:16]

Participants

5

Reactant 3

HCID 6328Methyl iodideHCID 11430Potassium CarbonateHCID 66684082HCID 66684082, compound

Product 1

HCID 66683883HCID 66683883, compoundYield 31.9%

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Procedure

To a solution of 5-(benzofuran-2-yl-hydroxy-methyl)-3-methoxy-2-(2,4,6-trimethyl-phenyl)-cyclopent-2-enone (1.11 g) in methanol (10 ml) is added potassium carbonate (476 mg), followed by methyl iodide (214 μl) and the resulting suspension heated to reflux for 17 hours. The crude reaction mixture is then concentrated in vacuuo and partitioned between ethyl acetate (50 ml) and water (50 ml) and the organic layer purified by automated flash chromatography to give 5-[1-benzofuran-2-yl-meth-(E)-ylidene]-3-methoxy-2-(2,4,6-trimethyl-phenyl)-cyclopent-2-enone (337 mg).

Workup

  1. temperaturethe resulting suspension heated
  2. temperatureto reflux for 17 hours
  3. customThe crude reaction mixture
  4. concentrationis then concentrated in vacuuo
  5. custompartitioned between ethyl acetate (50 ml) and water (50 ml)
  6. customthe organic layer purified by automated flash chromatography

Sources & evidence

ORD record
ord-b1deb0a547994f2cb3bd34677ab812a6
Source dataset
uspto-grants-2014_11
Patent number
US08889595B2

Reaction notes

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