Nitrogen → 1-[2-(tert-Butyl-dimethyl-silanyloxymethyl)-oxazol-4-yl]-ethanone

HRID 1044772Notes

Reaction equation

HRID 1044772 reaction equation
N#N.[C:3]([SiH2:7][O:8][C:9]([CH3:19])([CH3:18])[C:10]1[O:11][CH:12]=[C:13]([CH:15]([OH:17])[CH3:16])[N:14]=1)([CH3:6])([CH3:5])[CH3:4]>C(C#N)(C)=O.O=[Mn]=O>[C:3]([SiH2:7][O:8][C:9]([CH3:19])([CH3:18])[C:10]1[O:11][CH:12]=[C:13]([C:15](=[O:17])[CH3:16])[N:14]=1)([CH3:6])([CH3:4])[CH3:5]

Participants

5

Reactant 2

HCID 947NitrogenHCID 131730008HCID 131730008, compound

Product 1

HCID 1317300091-[2-(tert-Butyl-dimethyl-silanyloxymethyl)-oxazol-4-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-[2-(tert-butyl-dimethyl-silanyloxymethyl)-oxazol-4-yl]-ethanol (193 mg, 0.75 mmol) in AcCN (5.0 mL) was treated at rt with MnO2 (362 mg, 3.75 mmol). The reaction mixture was stirred for 16 h at rt before being filtered through Celite. The solvent was removed under reduced pressure to give the title compound as a white solid. TLC:rf (1:1 hept-EA)=0.69. LC-MS-conditions 02: tR=1.04 min, [M+H]+=255.84.

Workup

  1. filtrationbefore being filtered through Celite
  2. customThe solvent was removed under reduced pressure

Sources & evidence

ORD record
ord-0b8cfb2bda7b4bd384bb5c463dfb9457
Source dataset
uspto-grants-2013_10
Patent number
US08563714B2

Reaction notes

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