Methyl iodide → 7-Methoxymethoxy-3-(4-methoxymethoxyphenyl)-3-methylchroman-4-one

HRID 1268081Notes

Reaction equation

HRID 1268081 reaction equation
[CH3:1][O:2][CH2:3][O:4][C:5]1[CH:14]=[C:13]2[C:8]([C:9](=[O:25])[CH:10]([C:15]3[CH:20]=[CH:19][C:18]([O:21][CH2:22][O:23][CH3:24])=[CH:17][CH:16]=3)[CH2:11][O:12]2)=[CH:7][CH:6]=1.[C:26](=O)([O-])[O-].[K+].[K+].CI.CCCCCC.C(OCC)(=O)C>CC(C)=O.C(OCC)(=O)C>[CH3:1][O:2][CH2:3][O:4][C:5]1[CH:14]=[C:13]2[C:8]([C:9](=[O:25])[C:10]([C:15]3[CH:20]=[CH:19][C:18]([O:21][CH2:22][O:23][CH3:24])=[CH:17][CH:16]=3)([CH3:26])[CH2:11][O:12]2)=[CH:7][CH:6]=1

Participants

7

Reactant 4

HCID 6328Methyl iodideHCID 11430Potassium CarbonateHCID 21226206Ethyl acetate hexaneHCID 221236097-Methoxymethoxy-3-(4-methoxymethoxyphenyl)chroman-4-one

Product 1

HCID 154817637-Methoxymethoxy-3-(4-methoxymethoxyphenyl)-3-methylchroman-4-oneYield 82.2%

Reagents, catalysts & solvents 2

HCID 180AcetoneSolventHCID 8857Ethyl AcetateSolvent

Procedure

7-Methoxymethoxy-3-(4-methoxymethoxyphenyl)chroman-4-one(57.4 g, 0.167 mol) (see, Helv. Chim. Acta., 75, 2, 1992, 457-470) was dissolved in acetone(1100 ml), potassium carbonate(230 g, 1.67 mol) and methyl iodide(104 ml, 1.67 mol) were added thereto in order, and the resulting mixture was stirred for 5 days at room temperature. The reaction mixture was diluted with ethyl acetate and washed with water. The organic layer thus obtained was dried over magnesium sulfate, filtered, and concentrated under reduced pressure. The residue was purified by column chromatography(eluent:n-hexane/ethyl acetate=8/1, v/v) to give the title compound(49.2 g, Yield 82%) as a colorless oil.

Workup

  1. washwashed with water
  2. customThe organic layer thus obtained
  3. dry with materialwas dried over magnesium sulfate
  4. filtrationfiltered
  5. concentrationconcentrated under reduced pressure
  6. customThe residue was purified by column chromatography(eluent

Sources & evidence

ORD record
ord-856da83b721047de9c4873f09d74434c
Source dataset
uspto-grants-2003_04
Patent number
US06555571B2

Reaction notes

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