Dimethyl Sulfoxide → HCID 59283806, compound

HRID 1174454Notes

Reaction equation

HRID 1174454 reaction equation
CI.[CH:3]1[C:8]2=[C:9]3[C:17](=[CH:18][CH:19]=[C:7]2[CH:6]=[CH:5][CH:4]=1)[C:16]1C(=[CH:12][CH:13]=[C:14]2[CH:23]=[CH:22][CH:21]=[CH:20][C:15]2=1)C3.[CH3:24][C:25]([CH3:28])([O-])[CH3:26].[K+].CS(C)=O>O>[CH3:24][C:25]1([CH3:28])[C:9]2[C:17](=[CH:18][CH:19]=[C:7]3[CH:6]=[CH:5][CH:4]=[CH:3][C:8]3=2)[C:16]2[C:26]1=[CH:12][CH:13]=[C:14]1[CH:23]=[CH:22][CH:21]=[CH:20][C:15]1=2

Participants

6

Reactant 4

HCID 679Dimethyl SulfoxideHCID 6328Methyl iodide2×HCID 915913H-Dibenzo[a,g]fluoreneHCID 23665647Potassium tert-butoxide

Product 1

HCID 59283806HCID 59283806, compoundYield 50.1%

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Procedure

Methyl iodide 13.45 g (94.74 mmol) was dropwise added to a mixed solution of 8.41 g (31.58 mmol) of 13H-dibenzo[a,g]fluorene, 15.95 g (142.11 mmol) of potassium t-butoxide and 100 ml of dimethylsulfoxide at 20° C. in 20 minutes, and the solution was stirred for 8 hours. After left standing overnight, 13.45 g (94.74 mmol) of methyl iodide was further dropwise added and stirred for 11 hours. Water was dropwise added to the reaction mixture, and the solution was extracted twice with dichloromethane. After separating the solution, the organic phase was concentrated and refined by flash chromatograph (silica gel: hexane/dichloromethane=5/1) to obtain 4.66 g (yield: 50.1%) of 13,13-dimethyl-13H-dibenzo[a,g]fluorene.

Workup

  1. waitAfter left
  2. waitstanding overnight
  3. stirringstirred for 11 hours
  4. extractionthe solution was extracted twice with dichloromethane
  5. customAfter separating the solution
  6. concentrationthe organic phase was concentrated

Sources & evidence

ORD record
ord-ab89fbf8b51045cb81ff798599030356
Source dataset
uspto-grants-2010_11
Patent number
US07838130B2

Reaction notes

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