Triacetoxyperiodinane → HCID 57835736, compound

HRID 731201Notes

Reaction equation

HRID 731201 reaction equation
CC(OI1(OC(C)=O)(OC(C)=O)OC(=O)C2C=CC=CC1=2)=O.[O:23]1[C:27]([CH:28]([C:30]2[CH:35]=[CH:34][C:33]([O:36][CH:37]3[CH2:42][CH2:41][CH2:40][CH2:39][O:38]3)=[CH:32][CH:31]=2)[OH:29])=[CH:26][N:25]=[CH:24]1>C(Cl)Cl>[O:23]1[C:27]([C:28]([C:30]2[CH:31]=[CH:32][C:33]([O:36][CH:37]3[CH2:42][CH2:41][CH2:40][CH2:39][O:38]3)=[CH:34][CH:35]=2)=[O:29])=[CH:26][N:25]=[CH:24]1

Participants

4

Reactant 2

HCID 159087TriacetoxyperiodinaneHCID 57835730Oxazol-5-yl(4-(tetrahydro-2H-pyran-2-yloxy)phenyl)methanol

Product 1

HCID 57835736HCID 57835736, compoundYield 42%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

Dess-Martin periodinane (25 g, 60 mmol) was added to a solution of 75.1 (17 g crude, ˜50 mmol) in DCM (200 mL). After 1 hour, the reaction mixture was concentrated with silica gel and chromatographed (silica gel, 1:2 EtOAc/hexane) to obtain compound 75.2 (5.74 g, 21 mmol). MS ESI (pos.) m/e: 274.1 (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-7366ea8eb5ae4cf1892a780e2efeb851
Source dataset
uspto-grants-2009_09
Patent number
US07582803B2

Reaction notes

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