Acetic Acid → HCID 15518234, compound

HRID 635526Notes

Reaction equation

HRID 635526 reaction equation
[CH2:1]1[O:43][C:4]2=[CH:5][C:6]3[C:19]4[C:10](=[C:11]5[C:16](=[C:17]([CH2:20][CH2:21][CH2:22][CH2:23][O:24][Si](C(C)(C)C)(C)C)[N:18]=4)[C:15]([O:32][CH2:33][C:34]4[CH:39]=[CH:38][CH:37]=[CH:36][CH:35]=4)=[C:14]([O:40][CH3:41])[CH:13]=[CH:12]5)[CH:9]=[CH:8][C:7]=3[CH:42]=[C:3]2[O:2]1.C(O)(=O)C.[F-].C([N+](CCCC)(CCCC)CCCC)CCC>O1CCCC1>[CH2:1]1[O:43][C:4]2=[CH:5][C:6]3[C:19]4[C:10](=[C:11]5[C:16](=[C:17]([CH2:20][CH2:21][CH2:22][CH2:23][OH:24])[N:18]=4)[C:15]([O:32][CH2:33][C:34]4[CH:39]=[CH:38][CH:37]=[CH:36][CH:35]=4)=[C:14]([O:40][CH3:41])[CH:13]=[CH:12]5)[CH:9]=[CH:8][C:7]=3[CH:42]=[C:3]2[O:2]1

Participants

5

Reactant 3

HCID 176Acetic AcidHCID 2724141Tetrabutylammonium FluorideHCID 15518233HCID 15518233, compound

Product 1

HCID 15518234HCID 15518234, compoundYield 87%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

After 2,3-(methylenedioxy)-6-[4-(t-butyldimethylsiloxy)butyl]-7-benzyloxy-8-methoxy-benzo[c]phenanthridine (532 mg, 0.89 mmol) was dissolved in tetrahydrofuran (6 mL), acetic acid (102 μL, 1.78 mmol) and tetrabutylammonium fluoride (1M tetrahydrofuran solution, 1.78 mL) were added to the solution. The mixture was stirred at room temperature. The reaction solution was concentrated in vacuo. The residue was diluted with methylene chloride (30 mL), which was then washed with water. After the organic phase was dried over anhydrous sodium sulfate, the solvent was distilled off in vacuo. The residue was purified by silica gel column chromatography (eluted with 1% methanol-methylene chloride) to give 2,3-(methylenedioxy)-6-(4-hydroxybutyl)-7-benzyloxy-8-methoxy-benzo[c]phenanthridine (372 mg, yield 87%) as light yellow needles.

Workup

  1. concentrationThe reaction solution was concentrated in vacuo
  2. additionThe residue was diluted with methylene chloride (30 mL), which
  3. washwas then washed with water
  4. dry with materialAfter the organic phase was dried over anhydrous sodium sulfate
  5. distillationthe solvent was distilled off in vacuo
  6. customThe residue was purified by silica gel column chromatography (eluted with 1% methanol-methylene chloride)

Sources & evidence

ORD record
ord-ca791690ef204d6bbac029d9da9640eb
Source dataset
uspto-grants-2001_02
Patent number
US06187783B1

Reaction notes

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