Chlorotrimethylsilane → HCID 10624245, compound

HRID 1463258Notes

Reaction equation

HRID 1463258 reaction equation
Br[C:2]1[CH:7]=[CH:6][C:5]([O:8][Si:9]([C:12]([CH3:15])([CH3:14])[CH3:13])([CH3:11])[CH3:10])=[CH:4][CH:3]=1.C([Li])CCC.[Br:21][C:22]1[CH:23]=[C:24]([CH:27]=[O:28])[S:25][CH:26]=1.[CH3:29][Si:30](Cl)([CH3:32])[CH3:31]>C1COCC1.CCCCCC>[O:8]([C:5]1[CH:6]=[CH:7][C:2]([CH:27]([O:28][Si:30]([CH3:32])([CH3:31])[CH3:29])[C:24]2[S:25][CH:26]=[C:22]([Br:21])[CH:23]=2)=[CH:3][CH:4]=1)[Si:9]([C:12]([CH3:15])([CH3:14])[CH3:13])([CH3:11])[CH3:10]

Participants

7

Reactant 4

HCID 6397Chlorotrimethylsilane2×HCID 877924-Bromothiophene-2-carbaldehydeHCID 4227167(4-Bromophenoxy)(tert-butyl)dimethylsilaneHCID 178418339Butyllithium

Product 1

HCID 10624245HCID 10624245, compound

Reagents, catalysts & solvents 2

HCID 8028TetrahydrofuranSolvent2×HCID 8058HexaneSolvent

Procedure

5.9 gms (0.02 mol) of 4-bromo t-butyldimethylsiloxybenzene were dissolved in 42 ml of dry THF. The solution was cooled to -78° C. while under an argon atmosphere and 13.1 ml (0.02 mol) of a 1.6M solution of n-butyl lithium in hexane were added. After stirring for fifteen minutes under argon the solution was combined over a twenty-five-minute period with a solution of 4.0 gms (0.02 mol) of 4-bromo-2-thiophene carboxaldehyde in 50 ml. of THF at -78° C. The resulting solution was stirred for one hour and fifteen minutes at -78° C. 1.95 ml of trimethylsilylchloride (TMSCI) were added and the solution was allowed to warm to room temperature overnight with stirring. An additional 10 ml of TMSCl were added and the solution was stirred for six hours. The reaction was quenched with water; the organic phase was separated from the brine, dried over MgSO4, filtered, concentrated and separated by flash chromatography, utilizing hexane as the eluant. 2.5 gms of a clear colorless liquid were recovered having an NMR spectra of:

Workup

  1. additionwere added
  2. customat -78° C
  3. stirringThe resulting solution was stirred for one hour and fifteen minutes at -78° C
  4. stirringwith stirring
  5. stirringthe solution was stirred for six hours
  6. customThe reaction was quenched with water
  7. customthe organic phase was separated from the brine
  8. dry with materialdried over MgSO4
  9. filtrationfiltered
  10. concentrationconcentrated
  11. customseparated by flash chromatography
  12. custom2.5 gms of a clear colorless liquid were recovered

Sources & evidence

ORD record
ord-1cdf6e650363456da2da2d2527b6f57a
Source dataset
uspto-grants-1994_04
Patent number
US05300499

Reaction notes

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