Water → 5,7,9a-Trimethyl-8-methoxy-1,2,3,4,4a,9a-hexahydro-9fluorenone

HRID 2051411Notes

Reaction equation

HRID 2051411 reaction equation
[H-].[Na+].[CH3:3][C:4]1[CH:16]=[C:15]([CH3:17])[C:14]([O:18][CH3:19])=[C:13]2[C:5]=1[CH:6]1[CH:11]([C:12]2=[O:20])[CH2:10][CH2:9][CH2:8][CH2:7]1.[CH3:21]I.O>CN(C)C=O>[CH3:3][C:4]1[CH:16]=[C:15]([CH3:17])[C:14]([O:18][CH3:19])=[C:13]2[C:5]=1[CH:6]1[C:11]([CH3:21])([C:12]2=[O:20])[CH2:10][CH2:9][CH2:8][CH2:7]1

Participants

6

Reactant 4

HCID 962WaterHCID 6328Methyl iodideHCID 24758Sodium hydrideHCID 140437135,7-Dimethyl-8-methoxy-1,2,3,4,4a,9a-hexahydro-9-fluorenone

Product 1

HCID 151571875,7,9a-Trimethyl-8-methoxy-1,2,3,4,4a,9a-hexahydro-9fluorenone

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

3.42 Grams of 60% sodium hydride was gradually added to a solution prepared by dissolving 17.7 g of 5,7-dimethyl-8-methoxy-1,2,3,4,4a,9a-hexahydro-9-fluorenone in 100 ml of dimethylformamide under ice-cooling, followed by stirring at room temperature for 30 minutes. Then, 5.4 ml of methyl iodide was added thereto under ice-cooling, followed by stirring at room temperature for 1 hour. The reaction mixture was poured into 3 liters of water and extracted with chloroform. The organic layer was dried with magnesium sulfate and then the solvent was distilled off. The residue was purified by a silica gel column chromatography (eluent: ethyl acetate:n-hexane=1:20) to obtain 9.6 g of 5,7,9a-trimethyl-8-methoxy-1,2,3,4,4a,9a-hexahydro-9fluorenone. fluorenone.

Workup

  1. customprepared
  2. temperaturecooling
  3. temperatureunder ice-cooling
  4. stirringby stirring at room temperature for 1 hour
  5. extractionextracted with chloroform
  6. dry with materialThe organic layer was dried with magnesium sulfate
  7. distillationthe solvent was distilled off
  8. customThe residue was purified by a silica gel column chromatography (eluent: ethyl acetate:n-hexane=1:20)

Sources & evidence

ORD record
ord-66054ee41cde47fab46dd8d29cc24bc5
Source dataset
uspto-grants-1991_05
Patent number
US05017724

Reaction notes

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