Methyl iodide → HCID 21192686, compound

HRID 1067300Notes

Reaction equation

HRID 1067300 reaction equation
C[Mg]I.[Mg].[CH3:5]I.[CH:7]1([O:12][C:13]2[CH:20]=[CH:19][C:16]([CH:17]=[O:18])=[CH:15][C:14]=2[O:21][CH3:22])[CH2:11][CH2:10][CH2:9][CH2:8]1.[Cl-].[NH4+]>C(OCC)C.O1CCCC1>[C:17]([C:16]1[CH:19]=[CH:20][C:13]([O:12][CH:7]2[CH2:8][CH2:9][CH2:10][CH2:11]2)=[C:14]([O:21][CH3:22])[CH:15]=1)(=[O:18])[CH3:5]

Participants

8

Reactant 5

HCID 6328Methyl iodideHCID 25517Ammonium ChlorideHCID 31527214-Cyclopentyloxy-3-methoxy-benzaldehydeHCID 5462224MagnesiumHCID 178418373HCID 178418373, compound

Product 1

HCID 21192686HCID 21192686, compoundYield 73.6%

Reagents, catalysts & solvents 2

HCID 3283Diethyl EtherSolventHCID 8028TetrahydrofuranSolvent

Procedure

To a solution of methyl magnesium iodide, which is prepared from magnesium (2.9 g) and methyl iodide (7.5 ml), in diethyl ether (150 ml) is added dropwise a solution of 4-cyclopentyloxy-3-methoxybenzaldehyde (17.6 g) in tetrahydrofuran (40 ml) at 0° C., and the mixture is stirred at room temperature for one hour. To the reaction mixture is added a saturated aqueous ammonium chloride solution (20 ml) at 0° C., and the mixture is extracted with ethyl acetate. The extract is concentrated under reduced pressure, and the residue is dissolved in acetonitrile (300 ml), and thereto is added manganese dioxide (55 g) at 0° C. The mixture is warmed to room temperature, and the mixture is stirred for three days. To the reaction mixture is added cerite (20 g), and the mixture is stirred for 30 minutes. The insoluble materials are removed by filtration, and the filtrate is concentrated under reduced pressure. The residue is crystallized from chilled hexane to give 4-acetyl-1-cyclopentyloxy-2-methoxybenzene (13.8 g).

Workup

  1. extractionthe mixture is extracted with ethyl acetate
  2. concentrationThe extract is concentrated under reduced pressure
  3. dissolutionthe residue is dissolved in acetonitrile (300 ml)
  4. additionis added manganese dioxide (55 g) at 0° C
  5. temperatureThe mixture is warmed to room temperature
  6. stirringthe mixture is stirred for three days
  7. additionTo the reaction mixture is added cerite (20 g)
  8. stirringthe mixture is stirred for 30 minutes
  9. customThe insoluble materials are removed by filtration
  10. concentrationthe filtrate is concentrated under reduced pressure
  11. customThe residue is crystallized
  12. temperaturefrom chilled hexane

Sources & evidence

ORD record
ord-51c7a891861148d99c661eccb6432222
Source dataset
uspto-grants-2001_06
Patent number
US06248743B1

Reaction notes

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