Dimethylformamide → HCID 54329218, compound

HRID 1856945Notes

Reaction equation

HRID 1856945 reaction equation
[CH3:1][O:2][C:3]1[CH:4]=[C:5]([CH:11]=[C:12]2[C:16](=[O:17])[C:15]3[CH:18]=[CH:19][C:20]([OH:22])=[CH:21][C:14]=3[O:13]2)[CH:6]=[C:7]([O:9][CH3:10])[CH:8]=1.C(=O)([O-])[O-].[K+].[K+].CN(C)C=O.Br[CH:35]([CH3:37])[CH3:36]>O>[CH3:10][O:9][C:7]1[CH:6]=[C:5]([CH:11]=[C:12]2[C:16](=[O:17])[C:15]3[CH:18]=[CH:19][C:20]([O:22][CH:35]([CH3:37])[CH3:36])=[CH:21][C:14]=3[O:13]2)[CH:4]=[C:3]([O:2][CH3:1])[CH:8]=1

Participants

6

Reactant 4

HCID 6228DimethylformamideHCID 63582-BromopropaneHCID 11430Potassium CarbonateHCID 53855529HCID 53855529, compound

Product 1

HCID 54329218HCID 54329218, compoundYield 55.4%

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Procedure

To a solution of 2-[(3,5-dimethoxyphenyl)methylene]-6-hydroxy-3(2H)-benzofuranone 0.5 g, potassium carbonate 0.58 g and dimethylformamide 5 ml, 2-bromopropane 0.306 g was added. After the mixture was refluxed for 2.5 hours, water 50 ml was added. The resulting compound was extracted with ethyl acetate 50 ml twice. The ethyl acetate solution was dehydrated with anhydrous magnesium sulfate and concentrated under reduced pressure. The residue was fractionated by silica gel column chromatography (silica gel: 50 g, eluted with solvent 500 ml of hexane:ethyl acetate=1:1) and the fraction was concentrated to dryness at a temperature of 40° C. under reduced pressure to -obtain crystals. The crystals were dissolved in ethyl acetate 2 ml and hexane 10 ml, and the solution was allowed to stand at room temperature for four hours. The precipitated crystals were filtered and dried over phosphorous pentoxide at a temperature of 60° C. for four hours under reduced pressure to obtain the desired compound 316.1 mg.

Workup

  1. temperatureAfter the mixture was refluxed for 2.5 hours
  2. extractionThe resulting compound was extracted with ethyl acetate 50 ml twice
  3. concentrationconcentrated under reduced pressure
  4. washThe residue was fractionated by silica gel column chromatography (silica gel: 50 g, eluted with solvent 500 ml of hexane:ethyl acetate=1:1)
  5. concentrationthe fraction was concentrated to dryness at a temperature of 40° C. under reduced pressure to -obtain crystals
  6. dissolutionThe crystals were dissolved in ethyl acetate 2 ml
  7. filtrationThe precipitated crystals were filtered
  8. dry with materialdried over phosphorous pentoxide at a temperature of 60° C. for four hours under reduced pressure

Sources & evidence

ORD record
ord-fc9919c91a8e4f9aa035af5b710aa861
Source dataset
uspto-grants-2000_11
Patent number
US06143779

Reaction notes

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