Ethyl Acetate → HCID 67412867, compound

HRID 910169Notes

Reaction equation

HRID 910169 reaction equation
[OH:1][C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][C:3]=1[C:8](=[N:14][N:15]([CH3:17])[CH3:16])[N:9]1[CH:13]=[CH:12][N:11]=[CH:10]1.Cl[CH2:19][O:20][C:21]1[CH:26]=[CH:25][C:24]([Cl:27])=[CH:23][CH:22]=1.C(=O)([O-])[O-].[K+].[K+].C(OCC)(=O)C>CN(C)C=O>[Cl:27][C:24]1[CH:25]=[CH:26][C:21]([O:20][CH2:19][O:1][C:2]2[CH:7]=[CH:6][CH:5]=[CH:4][C:3]=2[C:8](=[N:14][N:15]([CH3:17])[CH3:16])[N:9]2[CH:13]=[CH:12][N:11]=[CH:10]2)=[CH:22][CH:23]=1

Participants

6

Reactant 4

HCID 8857Ethyl AcetateHCID 11430Potassium CarbonateHCID 88801alpha,4-DichloroanisoleHCID 136337079HCID 136337079, compound

Product 1

HCID 67412867HCID 67412867, compoundYield 63%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

To a solution of the Compound No. 13 (0.20 g, 0.869 mmol) obtained in Example 13 in N,N-dimethylformamide (3 ml) were added α,4-dichloroanisole (0.175 g, 0.989 mmol) and potassium carbonate (0.17 g, 1.23 mmol), and the mixture was stirred at room temperature for 20 hr. Ethyl acetate was added to the reaction mixture, the mixture was washed with water, and the organic layer was dried over sodium sulfate. The solvent was evaporated under reduced pressure, and the obtained residue was purified by silica gel column chromatography (hexane:ethyl acetate) to give the object compound (0.202 g, 0.545 mmol, yield 63%).

Workup

  1. washthe mixture was washed with water
  2. dry with materialthe organic layer was dried over sodium sulfate
  3. customThe solvent was evaporated under reduced pressure
  4. customthe obtained residue was purified by silica gel column chromatography (hexane:ethyl acetate)

Sources & evidence

ORD record
ord-8b743c0133bf40f388a5503170bd1cec
Source dataset
uspto-grants-2011_09
Patent number
US08022072B2

Reaction notes

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