Triacetoxyperiodinane → 1-(Dimethyl-1,3-thiazol-5-yl)-2-methylpropan-1-one
Reaction equation
CC(OI1(OC(C)=O)(OC(C)=O)OC(=O)C2C=CC=CC1=2)=O.[CH3:23][C:24]1[S:25][C:26]([CH:30]([OH:34])[CH:31]([CH3:33])[CH3:32])=[C:27]([CH3:29])[N:28]=1>C(Cl)Cl>[CH3:23][C:24]1[S:25][C:26]([C:30](=[O:34])[CH:31]([CH3:32])[CH3:33])=[C:27]([CH3:29])[N:28]=1Participants
4
Reactant 2
Product 1
Reagents, catalysts & solvents 1
Conditions
- Temperature
- 0 °C
Procedure
A flask containing Dess-Martin reagent (2.5 g, 5.89 mmol) in DCM (50 mL) was cooled to 0° C. and then a solution of 1-(2,4-dimethylthiazol-5-yl)-2-methylpropan-1-ol (830 mg, 4.48 mmol, Intermediate 4: step a) in DCM (10 mL) was added. After 5 minutes, the ice bath was removed and the reaction mixture was allowed to stir at room temperature for 45 minutes. The mixture was quenched with saturated aqueous NaHCO3 and 1 N aqueous NaOH (2 mL) 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. Chromatography on silica gel (10% EtOAc-DCM) afforded the title compound as a colorless oil.
Workup
- customthe ice bath was removed
- customThe mixture was quenched with saturated aqueous NaHCO3 and 1 N aqueous NaOH (2 mL)
- 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
Sources & evidence
- ORD record
- ord-deb5844731fe4ebe885695d9621d5d4b
- Source dataset
- uspto-grants-2016_05
- Patent number
- US09346782B2
Reaction notes
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