Triacetoxyperiodinane → (4-Chlorophenyl)(1-methyl-1H-1,2,3-triazol-5-yl)methanone
Reaction equation
CC(OI1(OC(C)=O)(OC(C)=O)OC(=O)C2C=CC=CC1=2)=O.[Cl:23][C:24]1[CH:29]=[CH:28][C:27]([CH:30]([C:32]2[N:36]([CH3:37])[N:35]=[N:34][CH:33]=2)[OH:31])=[CH:26][CH:25]=1>C(Cl)Cl>[Cl:23][C:24]1[CH:29]=[CH:28][C:27]([C:30]([C:32]2[N:36]([CH3:37])[N:35]=[N:34][CH:33]=2)=[O:31])=[CH:26][CH:25]=1Participants
Conditions
- Temperature
- 0 °C
Procedure
Similar to the procedure described in J. Am. Chem. Soc. 1991, 7277, a flask containing Dess-Martin reagent (1.50 g, 3.54 mmol) in DCM (30 mL) was cooled to 0° C. and then a solution of (4-chlorophenyl)(1-methyl-1H-1,2,3-triazol-5-yl)methanol (500 mg, 2.24 mmol, Intermediate 42, step b) in 10 mL of DCM was added. After 5 min, the ice bath was removed and the mixture was allowed to stir at room temperature for 45 min, at which time TLC (20% EtOAc-DCM) indicated the reaction was complete. The mixture was quenched with a saturated NaHCO3 solution and 2 mL of 1 N NaOH and the aqueous portion (pH ˜9) was extracted with DCM (3×75 mL). The combined organics were washed with brine, dried over MgSO4, filtered and concentrated to give a light amber solid. Flash chromatography on silica gel (10% EtOAc-DCM) afforded the title compound as a white solid.
Workup
- customthe ice bath was removed
- customThe mixture was quenched with a saturated NaHCO3 solution and 2 mL of 1 N NaOH
- extractionthe aqueous portion (pH ˜9) was extracted with DCM (3×75 mL)
- washThe combined organics were washed with brine
- dry with materialdried over MgSO4
- filtrationfiltered
- concentrationconcentrated
- customto give a light amber solid
Sources & evidence
- ORD record
- ord-fe3ed342d8bc45a4bb2625b173d47def
- Source dataset
- uspto-grants-2016_04
- Patent number
- US09309222B2
Reaction notes
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