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

HRID 927010Notes

Reaction equation

HRID 927010 reaction equation
[O:1]1[CH:5]=[CH:4][N:3]=[CH:2]1.C([Li])CCC.FC(F)(F)S(O[Si:17]([CH:24]([CH3:26])[CH3:25])([CH:21]([CH3:23])[CH3:22])[CH:18]([CH3:20])[CH3:19])(=O)=O>C(OCC)C>[CH:18]([Si:17]([CH:24]([CH3:26])[CH3:25])([CH:21]([CH3:23])[CH3:22])[C:2]1[O:1][CH:5]=[CH:4][N:3]=1)([CH3:20])[CH3:19]

Participants

5

Reactant 3

HCID 9255OxazoleHCID 2724529Triisopropylsilyl trifluoromethanesulfonateHCID 178418339Butyllithium

Product 1

HCID 595960162-(Tris(propan-2-yl)silyl)-1,3-oxazole

Reagents, catalysts & solvents 1

HCID 3283Diethyl EtherSolvent2×

Conditions

Temperature
-78 °C

Procedure

Oxazole (10 g, 144.797 mmol) is dissolved in 400 mL abs. diethylether under argon. The solution is cooled to −78° C. and n-butyllithium (1.6 M solution in hexane, 100 mL, 160 mmol) is added slowly at that temperature. After stirring for 1 h triisopropylsilyl trifluoromethanesulfonate (40.265 mL, 144.797 mmol) in 100 mL abs. diethylether is added slowly. The mixture is warmed to r.t. within 12 h, and the solvent is evaporated in vacuo. The residue is treated with cyclohexane, filtered over silica gel, washed with cylcohexane/ethyl acetate 8:1, and the solvent is evaporated in vacuo. Yield: 33 g; ESI mass spectrum: [M+H]+=226; retention time HPLC: 1.428 min (HPLC method Z001_002).

Workup

  1. temperatureThe mixture is warmed to r.t. within 12 h
  2. customthe solvent is evaporated in vacuo
  3. additionThe residue is treated with cyclohexane
  4. filtrationfiltered over silica gel
  5. washwashed with cylcohexane/ethyl acetate 8:1
  6. customthe solvent is evaporated in vacuo
  7. custom1.428 min (HPLC method Z001_002)

Sources & evidence

ORD record
ord-c16af105e7de458d9ac013c53fc037ff
Source dataset
uspto-grants-2016_03
Patent number
US09290457B2

Reaction notes

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