Oxazole → 2-(Tris(propan-2-yl)silyl)-1,3-oxazole

HRID 2264193Notes

Reaction equation

HRID 2264193 reaction equation
[Li]CCCC.[O:6]1[CH:10]=[CH:9][N:8]=[CH:7]1.O([Si:19]([CH:26]([CH3:28])[CH3:27])([CH:23]([CH3:25])[CH3:24])[CH:20]([CH3:22])[CH3:21])S(C(F)(F)F)(=O)=O>C(OCC)C>[CH:20]([Si:19]([CH:26]([CH3:28])[CH3:27])([CH:23]([CH3:25])[CH3:24])[C:7]1[O:6][CH:10]=[CH:9][N:8]=1)([CH3:22])[CH3:21]

Participants

5

Reactant 3

HCID 9255OxazoleHCID 2724529Triisopropylsilyl trifluoromethanesulfonateHCID 178418339Butyllithium

Product 1

HCID 595960162-(Tris(propan-2-yl)silyl)-1,3-oxazoleYield 93%

Reagents, catalysts & solvents 1

HCID 3283Diethyl EtherSolvent

Conditions

Temperature
-78 °C

Procedure

n-BuLi (1.6M in hexanes, 76 mL, 190 mmol) was added dropwise over 30 minutes to a stirred solution of oxazole (12.0 g, 174 mmol) in diethyl ether (400 mL) at −78° C. under argon. The solution was allowed to stir for 60 minutes at −78° C. and then triisopropylsilyl triflate (46.3 mL, 172 mmol) was added dropwise over 30 minutes. The reaction mixture was slowly warmed up to room temperature and stirred overnight. The mixture was concentrated in vacuo and the residue was taken up in hexanes and filtered through a pad of silica gel eluting with 8:1 hexanes/ethyl acetate. Concentration gave the title compound (36.0 g, 93%) as a colourless oil.

Workup

  1. temperatureThe reaction mixture was slowly warmed up to room temperature
  2. stirringstirred overnight
  3. concentrationThe mixture was concentrated in vacuo
  4. filtrationfiltered through a pad of silica gel eluting with 8:1 hexanes/ethyl acetate
  5. concentrationConcentration

Sources & evidence

ORD record
ord-534f55245b0246e3a6caadcc73407e2f
Source dataset
uspto-grants-2010_12
Patent number
US07855202B2

Reaction notes

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