Nitrogen → 1-(4-(((tert-Butyldimethylsilyl)oxy)methyl)oxazol-2-yl)ethanone

HRID 82819Notes

Reaction equation

HRID 82819 reaction equation
N#N.[Si:3]([O:10][CH2:11][C:12]1[N:13]=[C:14]([CH:17]([OH:19])[CH3:18])[O:15][CH:16]=1)([C:6]([CH3:9])([CH3:8])[CH3:7])([CH3:5])[CH3:4]>C(C#N)(C)=O.O=[Mn]=O>[Si:3]([O:10][CH2:11][C:12]1[N:13]=[C:14]([C:17](=[O:19])[CH3:18])[O:15][CH:16]=1)([C:6]([CH3:9])([CH3:7])[CH3:8])([CH3:5])[CH3:4]

Participants

5

Reactant 2

HCID 947NitrogenHCID 866982021-(4-(((tert-Butyldimethylsilyl)oxy)methyl)oxazol-2-yl)ethanol

Product 1

HCID 866982031-(4-(((tert-Butyldimethylsilyl)oxy)methyl)oxazol-2-yl)ethanone

Reagents, catalysts & solvents 2

HCID 14801Manganese dioxideCatalystHCID 694302-OxopropiononitrileSolvent

Procedure

In a flame dried round-bottomed flask equipped with a magnetic stir bar and under inert atmosphere (N2), a solution of 1-(4-(((tert-butyldimethylsilyl)oxy)methyl)oxazol-2-yl)ethanol (260 mg, 1.01 mmol) in AcCN (7.1 mL) was treated at rt with MnO2 (1488 mg, 5.05 mmol) and the resulting mixture was stirred overnight at rt. The reaction mixture was filtered and the solvent was removed under reduced pressure to give the title compound as a yellow oil. TLC: rf (2:1 hept-EA)=0.55. LC-MS-conditions 07: tR=0.96 min, [M]+=255.89.

Workup

  1. filtrationThe reaction mixture was filtered
  2. customthe solvent was removed under reduced pressure

Sources & evidence

ORD record
ord-bf4d6a8075d94de9b8fe4add6f42d80c
Source dataset
uspto-grants-2014_09
Patent number
US08846733B2

Reaction notes

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