Triacetoxyperiodinane → HCID 58065823, compound

HRID 1811503Notes

Reaction equation

HRID 1811503 reaction equation
CC(OI1(OC(C)=O)(OC(C)=O)OC(=O)C2C=CC=CC1=2)=O.[Br:23][C:24]1[CH:25]=[CH:26][C:27]2[N:28]([CH2:38][CH:39]([OH:48])[CH2:40][O:41][C:42]3[CH:47]=[CH:46][CH:45]=[CH:44][CH:43]=3)[C:29]3[C:34]([C:35]=2[CH:36]=1)=[CH:33][C:32]([Br:37])=[CH:31][CH:30]=3>ClCCl.CCOC(C)=O>[Br:23][C:24]1[CH:25]=[CH:26][C:27]2[N:28]([CH2:38][C:39](=[O:48])[CH2:40][O:41][C:42]3[CH:43]=[CH:44][CH:45]=[CH:46][CH:47]=3)[C:29]3[C:34]([C:35]=2[CH:36]=1)=[CH:33][C:32]([Br:37])=[CH:31][CH:30]=3

Participants

5

Reactant 2

HCID 159087TriacetoxyperiodinaneHCID 468517151-(3,6-dibromo-9H-carbazol-9-yl)-3-phenoxypropan-2-ol

Product 1

HCID 58065823HCID 58065823, compoundYield 74%

Reagents, catalysts & solvents 2

HCID 6344DichloromethaneSolventHCID 8857Ethyl AcetateSolvent

Procedure

Dess-Martin periodinane (58.2 mg, 0.137 mmol) was charged to a solution of the title compound of Example 3b (45.0 mg, 0.095 mmol) in dichloromethane (1.0 ml, 0.095 M). After two hours the reaction mixture was diluted with EtOAc and washed with saturated sodium thiosulfate solution, water and brine. The organic layer was dried over Na2SO4, filtered and condensed. The crude product was used without additional purification. Yield=74%

Workup

  1. washwashed with saturated sodium thiosulfate solution, water and brine
  2. dry with materialThe organic layer was dried over Na2SO4
  3. filtrationfiltered
  4. customcondensed
  5. customThe crude product was used without additional purification

Sources & evidence

ORD record
ord-839d594da7484b1f8f64397a6fd46b96
Source dataset
uspto-grants-2013_01
Patent number
US08362277B2

Reaction notes

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