Hexamethyldisilazane → HCID 54478909, compound

HRID 396838Notes

Reaction equation

HRID 396838 reaction equation
C[Si](C)(C)N[Si](C)(C)C.C([Li])CCC.[Si:15]([O:22][C:23]1[CH:28]=[CH:27][C:26]([C:29](=[O:31])[CH3:30])=[CH:25][C:24]=1[CH2:32][CH3:33])([C:18]([CH3:21])([CH3:20])[CH3:19])([CH3:17])[CH3:16].[F:34][C:35]([F:44])([F:43])[C:36](N1C=CN=C1)=[O:37]>C1COCC1>[Si:15]([O:22][C:23]1[CH:28]=[CH:27][C:26]([C:29](=[O:31])[CH2:30][C:36](=[O:37])[C:35]([F:44])([F:43])[F:34])=[CH:25][C:24]=1[CH2:32][CH3:33])([C:18]([CH3:21])([CH3:20])[CH3:19])([CH3:16])[CH3:17]

Participants

6

Reactant 4

HCID 13838HexamethyldisilazaneHCID 737671-(Trifluoroacetyl)imidazoleHCID 53924662HCID 53924662, compoundHCID 178418339Butyllithium

Product 1

HCID 54478909HCID 54478909, compoundYield 99%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent2×

Conditions

Temperature
0 °C

Procedure

To a stirred solution of 1,1,1,3,3,3-hexamethyldisilazane (1.79 g, 11.1 mmol) in THF (37 ml) was added n-butyl lithium (1.52 M solution in hexane; 7.3 ml, 11.1 mmol) dropwise at 0° C., and the mixture was stirred at 0° C. for 30 minutes, then cooled at −78° C. A solution of 1-(4-[[tert-butyl(dimethyl)silyl]oxy]-3-ethylphenyl)-1-ethanone (2.57 g, 9.23 mmol) in THF (40 ml) was added dropwise, and the mixture was stirred at −78° C. for 1 hour. 1-(Trifluoroacetyl)imidazole (2.0 g, 12.2 mmol) was added, and the mixture was stirred at −78° C. for 3 hours, and quenched with water. The reaction mixture was warmed up to room temperature, and diluted with ethyl acetate. The whole was extracted with ethyl acetate. The organic layer was washed with brine, dried over MgSO4, and concentrated in vacuo. The residue was used for next reaction without further purification. (3.45 g, 99% yield).

Workup

  1. temperaturecooled at −78° C
  2. stirringthe mixture was stirred at −78° C. for 1 hour
  3. stirringthe mixture was stirred at −78° C. for 3 hours
  4. customquenched with water
  5. temperatureThe reaction mixture was warmed up to room temperature
  6. additiondiluted with ethyl acetate
  7. extractionThe whole was extracted with ethyl acetate
  8. washThe organic layer was washed with brine
  9. dry with materialdried over MgSO4
  10. concentrationconcentrated in vacuo
  11. customThe residue was used for next reaction without further purification

Sources & evidence

ORD record
ord-9d09f79c556a43d2bab6428575478257
Source dataset
uspto-grants-2003_08
Patent number
US06608095B2

Reaction notes

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