Dimethylformamide → HCID 57682809, compound

HRID 495006Notes

Reaction equation

HRID 495006 reaction equation
CI.[CH2:3]([C:6]1[C:15]([OH:16])=[CH:14][CH:13]=[C:12]2[C:7]=1[CH2:8][CH2:9][C:10]([CH3:19])([CH3:18])[C:11]2=[O:17])[CH:4]=[CH2:5].[C:20](=O)([O-])[O-].[K+].[K+].CN(C)C=O>C(OCC)(=O)C.O>[CH2:3]([C:6]1[C:15]([O:16][CH3:20])=[CH:14][CH:13]=[C:12]2[C:7]=1[CH2:8][CH2:9][C:10]([CH3:19])([CH3:18])[C:11]2=[O:17])[CH:4]=[CH2:5]

Participants

7

Reactant 4

HCID 6228DimethylformamideHCID 6328Methyl iodideHCID 11430Potassium CarbonateHCID 57682852HCID 57682852, compound

Product 1

HCID 57682809HCID 57682809, compoundYield 96.9%

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 8857Ethyl AcetateSolvent

Procedure

575 μl of methyl iodide was added to a mixture consisting of 1.06 g of 5-allyl-6-hydroxy-2,2-dimethyl-3,4-dihydronaphthalen-1(2H)-one, 0.77 g of potassium carbonate, and 10 ml of N,N-dimethylformamide. The obtained mixture was stirred at room temperature under nitrogen atmosphere overnight. Water and ethyl acetate were added to the reaction solution, so as to obtain an organic layer. The obtained organic layer was washed with water (5 times) and a saturated sodium chloride solution, and then dried over anhydrous sodium sulfate. After removing the drying agent by filtration, the organic layer was concentrated under a reduced pressure. The residue was purified by silica gel column chromatography (hexane/ethyl acetate), so as to obtain 1.09 g of the subject compound.

Workup

  1. customso as to obtain an organic layer
  2. washThe obtained organic layer was washed with water (5 times)
  3. dry with materiala saturated sodium chloride solution, and then dried over anhydrous sodium sulfate
  4. customAfter removing the drying agent
  5. filtrationby filtration
  6. concentrationthe organic layer was concentrated under a reduced pressure
  7. customThe residue was purified by silica gel column chromatography (hexane/ethyl acetate)

Sources & evidence

ORD record
ord-824ac54536144ac7b621e090efc85f81
Source dataset
uspto-grants-2009_05
Patent number
US07538123B2

Reaction notes

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