Methyl iodide → 7-Allyloxy-5-methoxy-2,2-dimethyl-4-oxochromane

HRID 494958Notes

Reaction equation

HRID 494958 reaction equation
[CH2:1]([O:4][C:5]1[CH:14]=[C:13]2[C:8]([C:9](=[O:17])[CH2:10][C:11]([CH3:16])([CH3:15])[O:12]2)=[C:7]([OH:18])[CH:6]=1)[CH:2]=[CH2:3].[C:19](=O)([O-])[O-].[K+].[K+].IC>CN(C)C=O.C(OCC)(=O)C>[CH2:1]([O:4][C:5]1[CH:14]=[C:13]2[C:8]([C:9](=[O:17])[CH2:10][C:11]([CH3:15])([CH3:16])[O:12]2)=[C:7]([O:18][CH3:19])[CH:6]=1)[CH:2]=[CH2:3]

Participants

6

Reactant 3

HCID 6328Methyl iodideHCID 11430Potassium CarbonateHCID 576828337-Allyloxy-5-hydroxy-2,2-dimethyl-4-oxochromane

Product 1

HCID 576828717-Allyloxy-5-methoxy-2,2-dimethyl-4-oxochromaneYield 91.1%

Reagents, catalysts & solvents 2

HCID 6228DimethylformamideSolventHCID 8857Ethyl AcetateSolvent

Procedure

2.90 g of 7-allyloxy-5-hydroxy-2,2-dimethyl-4-oxochromane was dissolved in 50 ml of N,N-dimethylformamide. Thereafter, 2.42 g of potassium carbonate and 2.32 g of iodomethane were added to the reaction solution, and the obtained mixture was then stirred at room temperature for 3 days. Thereafter, the reaction solution was diluted with ethyl acetate. The resultant product was washed with 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 2.79 g of the subject compound.

Workup

  1. washThe resultant product was washed with a saturated sodium 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-80ae0aa5cdef48888a5237c1c7144cb8
Source dataset
uspto-grants-2009_05
Patent number
US07538123B2

Reaction notes

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