Triacetoxyperiodinane → (2,4-Dimethylthiazol-5-yl)(1-methyl-1H-1,2,3-triazol-5-yl)methanone

HRID 627519Notes

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]([C:32]2[N:36]([CH3:37])[N:35]=[N:34][CH:33]=2)[OH:31])=[C:27]([CH3:29])[N:28]=1>C(Cl)Cl>[CH3:23][C:24]1[S:25][C:26]([C:30]([C:32]2[N:36]([CH3:37])[N:35]=[N:34][CH:33]=2)=[O:31])=[C:27]([CH3:29])[N:28]=1

Participants

Conditions

Temperature: 0 °C

Procedure

A flask containing Dess-Martin reagent (7.50 g, 17.7 mmol) in DCM (200 mL) was cooled to 0° C. and then a solution of (2,4-dimethylthiazol-5-yl)(1-methyl-1H-1,2,3-triazol-5-yl)methanol (3.00 g, 13.4 mmol, Intermediate 45, step a) in 100 mL of DCM was added. After 5 min, the ice bath was removed and the reaction was allowed to stir at room temperature for 45 min, at which time TLC (30% acetone-DCM) indicated the reaction was complete. The reaction was quenched with saturated NaHCO3 solution and about 2 mL of 1 N NaOH and the aqueous portion (pH˜9) was extracted with DCM (3×75 mL). The combined organic layers were washed with brine, dried over MgSO4, filtered and concentrated to give an amber oil. Flash chromatography on silica gel (10-40% EtOAc-DCM) afforded the title compound as a yellow solid.

Workup

customthe ice bath was removed
customThe reaction was quenched with saturated NaHCO3 solution and about 2 mL of 1 N NaOH
extractionthe aqueous portion (pH˜9) was extracted with DCM (3×75 mL)
washThe combined organic layers were washed with brine
dry with materialdried over MgSO4
filtrationfiltered
concentrationconcentrated
customto give an amber oil

Sources & evidence

ORD record: ord-6dbc6706978d4eae9aadedf3be5b512f
Source dataset: uspto-grants-2016_04
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US09309222B2

Reaction notes

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