Dimethylformamide → HCID 57682775, compound

HRID 495002Notes

Reaction equation

HRID 495002 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][CH2:10][C:11]2=[O:17])[CH:4]=[CH2:5].[C:18](=O)([O-])[O-].[K+].[K+].CN(C)C=O>C(OCC)(=O)C.O>[CH2:3]([C:6]1[C:15]([O:16][CH3:18])=[CH:14][CH:13]=[C:12]2[C:7]=1[CH2:8][CH2:9][CH2:10][C:11]2=[O:17])[CH:4]=[CH2:5]

Participants

7

Reactant 4

HCID 6228DimethylformamideHCID 6328Methyl iodideHCID 11430Potassium CarbonateHCID 22324850HCID 22324850, compound

Product 1

HCID 57682775HCID 57682775, compoundYield 96.7%

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 8857Ethyl AcetateSolvent

Procedure

901 μl of methyl iodide was added to a mixture consisting of 1.46 g of 5-allyl-6-hydroxy-3,4-dihydronaphthalen-1(2H)-one, 1.20 g of potassium carbonate, and 15 ml of N,N-dimethylformamide. The obtained mixture was stirred at room temperature under nitrogen atmosphere overnight. Thereafter, water and ethyl acetate were added to the reaction solution, so as to separate an organic layer. The obtained organic layer was washed with water (5 times) and a saturated sodium chloride solution, and then dried over anhydrous magnesium 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 1.51 g of the subject compound.

Workup

  1. customso as to separate 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 magnesium 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-5383c035065b4b4ca3c07f42f3f4308f
Source dataset
uspto-grants-2009_05
Patent number
US07538123B2

Reaction notes

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