Methyl iodide → 8-Allyl-7-methoxy-2,2-dimethyl-4-oxochroman

HRID 494942Notes

Reaction equation

HRID 494942 reaction equation
[CH2:1]([C:4]1[C:5]([OH:17])=[CH:6][CH:7]=[C:8]2[C:13]=1[O:12][C:11]([CH3:15])([CH3:14])[CH2:10][C:9]2=[O:16])[CH:2]=[CH2:3].[C:18](=O)([O-])[O-].[K+].[K+].IC>CN(C)C=O.C(OCC)(=O)C>[CH2:1]([C:4]1[C:5]([O:17][CH3:18])=[CH:6][CH:7]=[C:8]2[C:13]=1[O:12][C:11]([CH3:14])([CH3:15])[CH2:10][C:9]2=[O:16])[CH:2]=[CH2:3]

Participants

6

Reactant 3

HCID 6328Methyl iodideHCID 11430Potassium CarbonateHCID 28180578-Allyl-7-hydroxy-2,2-dimethyl-4-oxochroman

Product 1

HCID 576828728-Allyl-7-methoxy-2,2-dimethyl-4-oxochromanYield 96.8%

Reagents, catalysts & solvents 2

HCID 6228DimethylformamideSolventHCID 8857Ethyl AcetateSolvent

Procedure

567 mg of 8-allyl-7-hydroxy-2,2-dimethyl-4-oxochroman was dissolved in 15 ml of N,N-dimethylformamide. Thereafter, 0.51 g of potassium carbonate and 0.42 g of iodomethane were added to the reaction solution, and the obtained mixture was then stirred at room temperature overnight. The reaction solution was diluted with ethyl acetate, and then washed with a saturated ammonium chloride aqueous solution and a saturated sodium chloride aqueous solution. The organic layer was dried over magnesium sulfate, and then concentrated under a reduced pressure. The residue was purified by silica gel column chromatography (hexane-ethyl acetate), so as to obtain 582 mg of the subject compound.

Workup

  1. washwashed with a saturated ammonium chloride aqueous solution
  2. dry with materialThe organic layer was dried over magnesium sulfate
  3. concentrationconcentrated under a reduced pressure
  4. customThe residue was purified by silica gel column chromatography (hexane-ethyl acetate)

Sources & evidence

ORD record
ord-0cf065ae28864bd7badd076a5eeaaf86
Source dataset
uspto-grants-2009_05
Patent number
US07538123B2

Reaction notes

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