Dimethylformamide → HCID 53865887, compound

HRID 1856948Notes

Reaction equation

HRID 1856948 reaction equation
[CH3:1][C:2]1[CH:3]=[C:4]([CH:10]=[C:11]2[C:15](=[O:16])[C:14]3[CH:17]=[CH:18][C:19]([OH:21])=[CH:20][C:13]=3[O:12]2)[CH:5]=[CH:6][C:7]=1[O:8][CH3:9].[C:22](=O)([O-])[O-].[K+].[K+].CN(C)C=O.C1(C)C=CC(S(OC)(=O)=O)=CC=1>C(OCC)(=O)C.CCCCCC.O>[CH3:1][C:2]1[CH:3]=[C:4]([CH:10]=[C:11]2[C:15](=[O:16])[C:14]3[CH:17]=[CH:18][C:19]([O:21][CH3:22])=[CH:20][C:13]=3[O:12]2)[CH:5]=[CH:6][C:7]=1[O:8][CH3:9]

Participants

8

Reactant 4

HCID 6228DimethylformamideHCID 6645Methyl p-toluenesulfonateHCID 11430Potassium CarbonateHCID 54283810HCID 54283810, compound

Product 1

HCID 53865887HCID 53865887, compoundYield 74.2%

Reagents, catalysts & solvents 3

HCID 962WaterSolventHCID 8058HexaneSolventHCID 8857Ethyl AcetateSolvent

Procedure

To a solution of 2-[(3-methyl-4-methoxyphenyl)methylene]-6-hydroxy-3(2H)-benzofuranone 0.477 g, potassium carbonate 0.583 g and dimethylformamide 5 ml, methyl p-toluenesulfonate 0.314 g was added. After the mixture was stirred for two hours at a temperature of 60° C., water 100 ml was added. The resulting compound 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, 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 371.6 mg.

Workup

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

Sources & evidence

ORD record
ord-d28b258b3fce4c308fa1896b0f555bbf
Source dataset
uspto-grants-2000_11
Patent number
US06143779

Reaction notes

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