Nitrogen → 4-(((tert-Butyldimethylsilyl)oxy)methyl)oxazole-2-carbaldehyde

HRID 82817Notes

Reaction equation

HRID 82817 reaction equation
N#N.[Si:3]([O:10][CH2:11][C:12]1[N:13]=[C:14](/[CH:17]=C/C2C=CC=CC=2)[O:15][CH:16]=1)([C:6]([CH3:9])([CH3:8])[CH3:7])([CH3:5])[CH3:4].[OH2:25]>CC(C)=O>[Si:3]([O:10][CH2:11][C:12]1[N:13]=[C:14]([CH:17]=[O:25])[O:15][CH:16]=1)([C:6]([CH3:7])([CH3:8])[CH3:9])([CH3:4])[CH3:5]

Participants

5

Reactant 3

HCID 947NitrogenHCID 962WaterHCID 67958594(E)-4-(((tert-Butyldimethylsilyl)oxy)methyl)-2-styryloxazole

Product 1

HCID 866982014-(((tert-Butyldimethylsilyl)oxy)methyl)oxazole-2-carbaldehyde

Reagents, catalysts & solvents 1

HCID 180AcetoneSolvent

Procedure

In a flame dried round-bottomed flask equipped with a magnetic stir bar and under inert atmosphere (N2), a solution of NaIO4 (726 mg, 3.33 mmol) in water (6.6) mL was slowly added to a vigorously stirred suspension of silica gel (4.46 g) in acetone (13.2 mL). The mixture was then concentrated under reduced pressure and the lumpy solid slurried in CH2Cl2 and the solvent was evaporated under reduced pressure. CH2Cl2 (16.5 mL) was added and the reaction mixture was treated at rt with (E)-4-(((tert-butyldimethylsilyl)oxy)methyl)-2-styryloxazole (350 mg, 1.1 mmol) and RuCl3 hydrate (7.8 mg, 0.03 mmol). The reaction mixture was stirred at rt in the dark overnight, filtered through silica gel and concentrated under reduced pressure to give the title compound as a red oil. TLC: rf (1:3 EA-Hept)=0.51. LC-MS-conditions 07: tR=0.64 min.

Workup

  1. concentrationThe mixture was then concentrated under reduced pressure
  2. customthe lumpy solid slurried in CH2Cl2 and the solvent was evaporated under reduced pressure
  3. additionCH2Cl2 (16.5 mL) was added
  4. filtrationfiltered through silica gel
  5. concentrationconcentrated under reduced pressure

Sources & evidence

ORD record
ord-1bc15eeb40b944a997987df4e14917ad
Source dataset
uspto-grants-2014_09
Patent number
US08846733B2

Reaction notes

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