Dimethyl Sulfoxide → HCID 53966917, compound

HRID 1174452Notes

Reaction equation

HRID 1174452 reaction equation
CI.[CH:3]1[C:19]2[C:18]3CC4[C:15]5[CH:20]=[CH:21][CH:22]=[CH:23][C:14]=5[CH:13]=[CH:12][C:11]=4[C:10]=3[CH:9]=[CH:8][C:7]=2[CH:6]=[CH:5][CH:4]=1.[CH3:24][C:25]([CH3:28])([O-])[CH3:26].[K+].CS(C)=O>O>[CH3:24][C:25]1([CH3:28])[C:18]2[C:19]3[CH:3]=[CH:4][CH:5]=[CH:6][C:7]=3[CH:8]=[CH:9][C:10]=2[C:11]2[CH:12]=[CH:13][C:14]3[CH:15]=[CH:20][CH:21]=[CH:22][C:23]=3[C:26]1=2

Participants

6

Reactant 4

HCID 679Dimethyl SulfoxideHCID 6328Methyl iodide2×HCID 13618583239-60-1HCID 23665647Potassium tert-butoxide

Product 1

HCID 53966917HCID 53966917, compoundYield 58.7%

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Procedure

Methyl iodide 9.88 g (69.6 mmol) was dropwise added to a mixed solution of 6.18 g (23.2 mmol) of 13H-dibenzo[a,i]fluorene, 11.72 g (104.4 mmol) of potassium t-butoxide and 100 ml of dimethylsulfoxide at 20° C. in 20 minutes, and the solution was stirred for 10 hours. After left standing overnight, 9.88 g (69.6 mmol) of methyl iodide was further dropwise added and stirred for 5 hours. Water was dropwise added to the reaction mixture, and the solution was extracted with dichloromethane. After separating the solution, the organic phase was concentrated and refined by flash chromatograph (silica gel: hexane/dichloromethane=5/1) to obtain 4.01 g (yield: 58.7%) of 13,13-dimethyl-13H-dibenzo[a,i]fluorene.

Workup

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

Sources & evidence

ORD record
ord-9e398de0eb034ba1912032b877c9915b
Source dataset
uspto-grants-2010_11
Patent number
US07838130B2

Reaction notes

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