Dimethylformamide → HCID 89586186, compound

HRID 1747775Notes

Reaction equation

HRID 1747775 reaction equation
[C:1]([C:4]1[O:5][C:6]([C:12]2[CH:17]=[CH:16][CH:15]=[CH:14][CH:13]=2)=[CH:7][C:8](=[O:11])[C:9]=1[OH:10])(=[O:3])[CH3:2].[C:18](=O)([O-])[O-].[K+].[K+].IC.CN(C=O)C>O>[C:1]([C:4]1[O:5][C:6]([C:12]2[CH:17]=[CH:16][CH:15]=[CH:14][CH:13]=2)=[CH:7][C:8](=[O:11])[C:9]=1[O:10][CH3:18])(=[O:3])[CH3:2]

Participants

6

Reactant 4

HCID 6228DimethylformamideHCID 6328Methyl iodideHCID 11430Potassium CarbonateHCID 132009232-Acetyl-3-hydroxy-6-phenyl-4H-pyran-4-one

Product 1

HCID 89586186HCID 89586186, compoundYield 42.4%

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Procedure

A mixture of 2-acetyl-3-hydroxy-6-phenyl-4H-pyran-4-one (200 mg), potassium carbonate (150 mg), iodomethane (0.0600 mL) and DMF (5.0 mL) was stirred at room temperature overnight. The reaction mixture was diluted with water and the mixture was extracted with ethyl acetate. The extract was dried over anhydrous sodium sulfate, and concentrated under reduced pressure. The residue was purified by silica gel column chromatography (ethyl acetate/hexane) to give the title compound (90.0 mg).

Workup

  1. extractionthe mixture was extracted with ethyl acetate
  2. dry with materialThe extract was dried over anhydrous sodium sulfate
  3. concentrationconcentrated under reduced pressure
  4. customThe residue was purified by silica gel column chromatography (ethyl acetate/hexane)

Sources & evidence

ORD record
ord-d92a07a2721e42a08216311e32d3366b
Source dataset
uspto-grants-2015_10
Patent number
US09150588B2

Reaction notes

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