Dimethylformamide → HCID 624632, compound

HRID 1856949Notes

Reaction equation

HRID 1856949 reaction equation
[CH3:1][O:2][C:3]1[CH:4]=[C:5]([CH:9]=[C:10]2[C:14](=[O:15])[C:13]3[CH:16]=[CH:17][C:18]([OH:20])=[CH:19][C:12]=3[O:11]2)[CH:6]=[CH:7][CH:8]=1.[C:21](=O)([O-])[O-].[K+].[K+].CN(C)C=O.CC1C=CC(S(C)(=O)=O)=CC=1>C(OCC)(=O)C.CCCCCC.O>[CH3:1][O:2][C:3]1[CH:4]=[C:5]([CH:9]=[C:10]2[C:14](=[O:15])[C:13]3[CH:16]=[CH:17][C:18]([O:20][CH3:21])=[CH:19][C:12]=3[O:11]2)[CH:6]=[CH:7][CH:8]=1

Participants

8

Reactant 4

HCID 6228DimethylformamideHCID 11430Potassium CarbonateHCID 18521p-Tolyl methyl sulfoneHCID 3563475HCID 3563475, compound

Product 1

HCID 624632HCID 624632, compoundYield 79.3%

Reagents, catalysts & solvents 3

HCID 962WaterSolventHCID 8058HexaneSolventHCID 8857Ethyl AcetateSolvent

Procedure

To a solution of 2-[(3-methoxyphenyl)methylene]-6-hydroxy-3(2H)-benzofuranone 0.452 g, potassium carbonate 0.583 g and dimethylformamide 5 ml, methyl p-toluene sulfonate 0.314 g was added. After the mixture was stirred for two hours at a temperature of 60° C., water 100 ml was added, and the mixture was extracted with ethyl acetate 50 ml twice. The ethyl acetate solution was washed with a saturated sodium chloride solution 50 ml twice, dehydrated with anhydrous magnesium sulfate, filtered and concentrated at a temperature of 40° C. under reduced pressure to obtain crude powder. 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 two 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 377.2 mg.

Workup

  1. additionwas added
  2. extractionthe mixture was extracted with ethyl acetate 50 ml twice
  3. washThe ethyl acetate solution was washed with a saturated sodium chloride solution 50 ml twice
  4. filtrationfiltered
  5. concentrationconcentrated at a temperature of 40° C. under reduced pressure
  6. customto obtain crude powder
  7. washThe residue was fractionated by silica gel column chromatography (silica gel: 50 g, eluted with solvent 500 ml of hexane:ethyl acetate=1:1)
  8. concentrationthe fraction was concentrated to dryness at a temperature of 40° C. under reduced pressure
  9. customto obtain crystals
  10. filtrationThe precipitated crystals were filtered
  11. dry with materialdried over phosphorous pentoxide at a temperature of 60° C. for four hours under reduced pressure

Sources & evidence

ORD record
ord-3781edfa60784806849a1e5d05c249b1
Source dataset
uspto-grants-2000_11
Patent number
US06143779

Reaction notes

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