HCID 15518232, compound → HCID 15518233, compound

HRID 635525Notes

Reaction equation

HRID 635525 reaction equation
[CH2:1]1[O:44][C:4]2=[CH:5][C:6]3[C:19]4[N:18](C)[CH:17]([CH2:21][CH2:22][CH2:23][CH2:24][O:25][Si:26]([C:29]([CH3:32])([CH3:31])[CH3:30])([CH3:28])[CH3:27])[C:16]5[C:11](=[CH:12][CH:13]=[C:14]([O:41][CH3:42])[C:15]=5[O:33][CH2:34][C:35]5[CH:40]=[CH:39][CH:38]=[CH:37][CH:36]=5)[C:10]=4[CH:9]=[CH:8][C:7]=3[CH:43]=[C:3]2[O:2]1>C1(C)C=CC=CC=1.CO.C(Cl)Cl.[O-2].[O-2].[Mn+4]>[CH2:1]1[O:44][C:4]2=[CH:5][C:6]3[C:19]4[C:10](=[C:11]5[C:16](=[C:17]([CH2:21][CH2:22][CH2:23][CH2:24][O:25][Si:26]([C:29]([CH3:31])([CH3:30])[CH3:32])([CH3:28])[CH3:27])[N:18]=4)[C:15]([O:33][CH2:34][C:35]4[CH:36]=[CH:37][CH:38]=[CH:39][CH:40]=4)=[C:14]([O:41][CH3:42])[CH:13]=[CH:12]5)[CH:9]=[CH:8][C:7]=3[CH:43]=[C:3]2[O:2]1

Participants

5

Reactant 1

HCID 15518232HCID 15518232, compound

Product 1

HCID 15518233HCID 15518233, compoundYield 70.2%

Reagents, catalysts & solvents 3

HCID 178418406HCID 178418406, compoundCatalystHCID 1140TolueneSolventHCID 21226129Dichloromethane methanolSolvent

Procedure

After 2,3-(methylenedioxy)-5-methyl-6-[4-(t-butyldimethylsiloxy)butyl]-7-benzyloxy-8-methoxy-5,6-dihydrobenzo[c]phenanthridine (300 mg, 0.49 mmol) was dissolved in toluene (8 mL), activated manganese dioxide (1.5 g) was added to the solution. The mixture was heated to reflux for an hour. After cooling to room temperature, the reaction mixture was diluted with a 10% methanol-methylene chloride solution (12 mL) followed by filtration. The filtrate was concentrated in vacuo. The resulting residue was purified by silica gel column chromatography (eluted with methylene chloride) to provide 2,3-(methylenedioxy)-6-[4-(t-butyldimethylsiloxy)butyl]-7-benzyloxy-8-methoxy-benzo[c]phenanthridine (205 mg, yield 70%) as light brown crystals.

Workup

  1. temperatureThe mixture was heated
  2. temperatureto reflux for an hour
  3. filtrationfollowed by filtration
  4. concentrationThe filtrate was concentrated in vacuo
  5. customThe resulting residue was purified by silica gel column chromatography (eluted with methylene chloride)

Sources & evidence

ORD record
ord-11815cc31b9047ca9cf97de67531fed7
Source dataset
uspto-grants-2001_02
Patent number
US06187783B1

Reaction notes

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