Ammonium Chloride → HCID 15518231, compound

HRID 635522Notes

Reaction equation

HRID 635522 reaction equation
[Mg].[O:2]([CH2:10][CH2:11][CH2:12]Br)[Si:3]([C:6]([CH3:9])([CH3:8])[CH3:7])([CH3:5])[CH3:4].[CH2:14]1[O:48][C:17]2=[CH:18][C:19]3[C:32]4[N:31]([CH3:33])[CH:30](OCC)[C:29]5[C:24](=[CH:25][CH:26]=[C:27]([O:45][CH3:46])[C:28]=5[O:37][CH2:38][C:39]5[CH:44]=[CH:43][CH:42]=[CH:41][CH:40]=5)[C:23]=4[CH:22]=[CH:21][C:20]=3[CH:47]=[C:16]2[O:15]1.[Cl-].[NH4+]>O1CCCC1.II.BrCCBr>[CH2:14]1[O:48][C:17]2=[CH:18][C:19]3[C:32]4[N:31]([CH3:33])[CH:30]([CH2:12][CH2:11][CH2:10][O:2][Si:3]([C:6]([CH3:9])([CH3:8])[CH3:7])([CH3:5])[CH3:4])[C:29]5[C:24](=[CH:25][CH:26]=[C:27]([O:45][CH3:46])[C:28]=5[O:37][CH2:38][C:39]5[CH:44]=[CH:43][CH:42]=[CH:41][CH:40]=5)[C:23]=4[CH:22]=[CH:21][C:20]=3[CH:47]=[C:16]2[O:15]1

Participants

8

Reactant 4

HCID 25517Ammonium ChlorideHCID 607486(3-Bromopropoxy)(tert-butyl)dimethylsilaneHCID 5462224MagnesiumHCID 15390591HCID 15390591, compound

Product 1

HCID 15518231HCID 15518231, compoundYield 96%

Reagents, catalysts & solvents 3

HCID 78391,2-DibromoethaneCatalystHCID 807IodineSolventHCID 8028TetrahydrofuranSolvent3×

Procedure

In a dry flask, a piece of magnesium (0.468 g, 19.3 mmols) was charged, and tetrahydrofuran (15 mL) was added thereto. A solution of 3-(t-butyldimethylsiloxy)propyl bromide (2.36 g, 9.63 mmols) in tetrahydrofuran (15 mL), iodine (a few pieces) and 1,2-dibromoethane (a few drops) were added portionwise to the mixture. The resulting mixture was stirred at room temperature for an hour. A solution of 2,3-(methylenedioxy)-5-methyl-6-ethoxy-7-benzyloxy-8-methoxy-5,6-dihydrobenzo[c]phenanthridine (1.01 g, 2,2 mmols) in tetrahydrofuran (10 mL) was added to the resulting solution followed by stirring at room temperature for 2 hours. A saturated ammonium chloride aqueous solution was added to the reaction mixture followed by extracting with ethyl acetate. The organic layer was separated, washed with saturated sodium chloride aqueous solution and then dried over anhydrous sodium sulfate. After sodium sulfate was removed by filtration, the solvent was distilled off in vacuo. The resulting residue was purified by silica gel column chromatography (eluted with 33-66% methylene chloride-hexane) to give 2,3-(methylenedioxy)-5-methyl-6-[3-(t-butyldimethylsiloxy)propyl]-7-benzyloxy-8-methoxy-5,6-dihydrobenzo[c]phenanthridine (1.12 g, yield 96%) as colorless amorphous solid.

Workup

  1. stirringby stirring at room temperature for 2 hours
  2. extractionby extracting with ethyl acetate
  3. customThe organic layer was separated
  4. washwashed with saturated sodium chloride aqueous solution
  5. dry with materialdried over anhydrous sodium sulfate
  6. customAfter sodium sulfate was removed by filtration
  7. distillationthe solvent was distilled off in vacuo
  8. customThe resulting residue was purified by silica gel column chromatography (eluted with 33-66% methylene chloride-hexane)

Sources & evidence

ORD record
ord-73e1c3186e4a4c3cb808ab7796047253
Source dataset
uspto-grants-2001_02
Patent number
US06187783B1

Reaction notes

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