Triacetoxyperiodinane → HCID 58065823, compound

HRID 404302Notes

Reaction equation

HRID 404302 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-20d2c62c2a124c65ad72b14e8983463e
Source dataset
uspto-grants-2014_06
Patent number
US08748473B2

Reaction notes

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