Dimethylformamide → methyl 4-methyl-9-oxo-9H-fluorene-2-carboxylate

HRID 541142Notes

Reaction equation

HRID 541142 reaction equation
[CH3:1][C:2]1[C:14]2[C:13]3[C:8](=[CH:9][CH:10]=[CH:11][CH:12]=3)[C:7](=[O:15])[C:6]=2[CH:5]=[C:4]([C:16]([OH:18])=[O:17])[CH:3]=1.[C:19](=O)([O-])[O-].[K+].[K+].CN(C)C=O.CI>O>[CH3:1][C:2]1[C:14]2[C:13]3[C:8](=[CH:9][CH:10]=[CH:11][CH:12]=3)[C:7](=[O:15])[C:6]=2[CH:5]=[C:4]([C:16]([O:18][CH3:19])=[O:17])[CH:3]=1

Participants

6

Reactant 4

HCID 6228DimethylformamideHCID 6328Methyl iodideHCID 11430Potassium CarbonateHCID 594925644-methyl-9-oxo-9H-fluorene-2-carboxylic acid

Product 1

HCID 59492531methyl 4-methyl-9-oxo-9H-fluorene-2-carboxylateYield 96.2%

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Procedure

Under anhydrous calcium chloride drying conditions, 4-methyl-9-oxo-9H-fluorene-2-carboxylic acid (1.745 g), potassium carbonate (3.03 g) and dimethylformamide (20 ml) were mixed. To this mixture was added methyl iodide (0.92 ml) at room temperature, and the mixture was stirred for 3 hr 15 min. To the reaction mixture was added water (60 ml), and the mixture was stirred at room temperature for 30 min. The mixture was filtered and the obtained solid was air-dried and dried under reduced pressure at 80° C. to give the title compound (1.778 g, 96%).

Workup

  1. stirringthe mixture was stirred at room temperature for 30 min
  2. filtrationThe mixture was filtered
  3. customthe obtained solid was air-dried
  4. customdried under reduced pressure at 80° C.

Sources & evidence

ORD record
ord-5c93f162cac6468881f8fa88d7478290
Source dataset
uspto-grants-2014_10
Patent number
US08871934B2

Reaction notes

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