Dimethylformamide → HCID 57682888, compound

HRID 495004Notes

Reaction equation

HRID 495004 reaction equation
[CH2:1](Br)[CH:2]=[CH2:3].O[C:6]1[CH:7]=[C:8]2[C:13](=[CH:14][CH:15]=1)[C:12](=[O:16])[CH2:11][CH2:10][CH2:9]2.[C:17](=[O:20])([O-])[O-].[K+].[K+].[CH3:23]N(C)C=O>C(OCC)(=O)C.O>[CH2:1]([O:16][C:12]1[CH:13]=[C:8]2[C:9](=[CH:10][CH:11]=1)[C:17](=[O:20])[C:15]([CH3:14])([CH3:23])[CH2:6][CH2:7]2)[CH:2]=[CH2:3]

Participants

7

Reactant 4

HCID 6228DimethylformamideHCID 7841Allyl bromideHCID 11430Potassium CarbonateHCID 46794946-Hydroxy-3,4-dihydro-1(2H)-naphthalenone

Product 1

HCID 57682888HCID 57682888, compound

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 8857Ethyl AcetateSolvent

Procedure

830 μl of allyl bromide was added to a mixture consisting of 1.52 g of 6-hydroxy-3,4-dihydronaphthalen-1(2H)-one, 1.22 g of potassium carbonate, and 15 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 successively washed with water (4 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 1.69 g of the subject compound.

Workup

  1. customso as to obtain an organic layer
  2. washThe obtained organic layer was successively washed with water (4 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-6e2a0e0103ad4123838cbe4337287dea
Source dataset
uspto-grants-2009_05
Patent number
US07538123B2

Reaction notes

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