Chlorotrimethylsilane → 2-(Trimethylsilyl)-1,3-oxazole

HRID 373498Notes

Reaction equation

HRID 373498 reaction equation
C([Li])CCC.[O:6]1[CH:10]=[CH:9][N:8]=[CH:7]1.[CH3:11][Si:12](Cl)([CH3:14])[CH3:13]>CCCCCC.CCOCC>[CH3:11][Si:12]([CH3:14])([CH3:13])[C:7]1[O:6][CH:10]=[CH:9][N:8]=1

Participants

6

Reactant 3

HCID 6397ChlorotrimethylsilaneHCID 9255OxazoleHCID 178418339Butyllithium

Product 1

HCID 147866212-(Trimethylsilyl)-1,3-oxazoleYield 50.1%

Reagents, catalysts & solvents 2

HCID 3283Diethyl EtherSolventHCID 8058HexaneSolvent

Procedure

n-Butyllithium (28.5 ml of a 2.54M solution in hexane) was added to a -78° solution of oxazole (5.0 g) in ether (150 ml). The resulting solution was stirred at -78° for 30 min, followed by the addition of trimethylsilyl chloride (7.86 g), and the mixture allowed to warm to room temperature. The reaction mixture was distilled and the fraction with a boiling point of about 130° was collected to afford 2-trimethylsilyl oxazole (5.12 g); MS, m/e=142(M+1), 91, 73.

Workup

  1. distillationThe reaction mixture was distilled
  2. customthe fraction with a boiling point of about 130° was collected

Sources & evidence

ORD record
ord-f4f3679e7afc402c9670274801d0f840
Source dataset
uspto-grants-1992_11
Patent number
US05164371

Reaction notes

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