Dimethylformamide → HCID 89586183, compound

HRID 1747782Notes

Reaction equation

HRID 1747782 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(=O)([O-])[O-].[K+].[K+].[CH2:24](Br)[C:25]1[CH:30]=[CH:29][CH:28]=[CH:27][CH:26]=1.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][CH2:24][C:25]1[CH:30]=[CH:29][CH:28]=[CH:27][CH:26]=1)(=[O:3])[CH3:2]

Participants

6

Reactant 4

HCID 6228DimethylformamideHCID 7498Benzyl BromideHCID 11430Potassium CarbonateHCID 132009232-Acetyl-3-hydroxy-6-phenyl-4H-pyran-4-one

Product 1

HCID 89586183HCID 89586183, compound

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Procedure

A mixture of 2-acetyl-3-hydroxy-6-phenyl-4H-pyran-4-one (0.53 g), potassium carbonate (0.40 g), benzyl bromide (0.27 mL) and DMF (10 mL) was stirred at room temperature for 2 hr. The reaction mixture was diluted with water, and 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 (0.18 g).

Workup

  1. extractionextracted 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-3bcc3a1ecbb14c5283116a1dc7888b5e
Source dataset
uspto-grants-2015_10
Patent number
US09150588B2

Reaction notes

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