Triacetoxyperiodinane → (4-(Benzyloxy)phenyl)(3-methyl-3H-1,2,3-triazol-4-yl)methanone

HRID 731191Notes

Reaction equation

HRID 731191 reaction equation
CC(OI1(OC(C)=O)(OC(C)=O)OC(=O)C2C=CC=CC1=2)=O.[CH2:23]([O:30][C:31]1[CH:36]=[CH:35][C:34]([CH:37]([C:39]2[N:40]([CH3:44])[N:41]=[N:42][CH:43]=2)[OH:38])=[CH:33][CH:32]=1)[C:24]1[CH:29]=[CH:28][CH:27]=[CH:26][CH:25]=1>C(Cl)Cl>[CH2:23]([O:30][C:31]1[CH:36]=[CH:35][C:34]([C:37]([C:39]2[N:40]([CH3:44])[N:41]=[N:42][CH:43]=2)=[O:38])=[CH:33][CH:32]=1)[C:24]1[CH:25]=[CH:26][CH:27]=[CH:28][CH:29]=1

Participants

4

Reactant 2

HCID 159087TriacetoxyperiodinaneHCID 57835740(4-(Benzyloxy)phenyl)(3-methyl-3H-1,2,3-triazol-4-yl)methanol

Product 1

HCID 57835886(4-(Benzyloxy)phenyl)(3-methyl-3H-1,2,3-triazol-4-yl)methanoneYield 94.8%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

Dess-Martin periodinane (8 g, 19 mmol) was added to a solution of 73.2 (˜15.5 mmol) in DCM (80 mL). After 1 hour, the reaction mixture was concentrated with silica gel and chromatographed (silica gel, 1:2 EtOAc/hexane) to obtain compound 73.3 (4.3 g, 14.7 mmol). MS ESI (pos.) m/e: 294.1 (M+H).

Workup

  1. concentrationthe reaction mixture was concentrated with silica gel
  2. customchromatographed (silica gel, 1:2 EtOAc/hexane)

Sources & evidence

ORD record
ord-a9c2fbf2e3234681bb3e15038a7a00d7
Source dataset
uspto-grants-2009_09
Patent number
US07582803B2

Reaction notes

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