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Chlorotrimethylsilane → 1-(2,5-Dimethyl-3-furyl)-1-(4-methyl-5-thiazolyl)ethanol

HRID 2816
Notes
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Reaction equation

HRID 2816 reaction equation
[CH3:1][C:2]1[N:3]=[CH:4][S:5][CH:6]=1.C([Li])CCC.C[Si](Cl)(C)C.[C:17]([C:20]1[CH:24]=[C:23]([CH3:25])[O:22][C:21]=1[CH3:26])(=[O:19])[CH3:18].C(=O)([O-])O.[Na+]>O1CCCC1>[CH3:26][C:21]1[O:22][C:23]([CH3:25])=[CH:24][C:20]=1[C:17]([C:6]1[S:5][CH:4]=[N:3][C:2]=1[CH3:1])([OH:19])[CH3:18]
ParticipantsConditionsProcedureWorkupSources & evidenceReaction notes

Participants

7

Reactant 5

HCID 6397ChlorotrimethylsilaneHCID 127484-MethylthiazoleHCID 615273-Acetyl-2,5-dimethylfuranHCID 516892Sodium BicarbonateHCID 178418339Butyllithium2×

Product 1

HCID 189362891-(2,5-Dimethyl-3-furyl)-1-(4-methyl-5-thiazolyl)ethanol

Reagents, catalysts & solvents

1
HCID 8028TetrahydrofuranSolvent

Conditions

Temperature
-70 °C

Procedure

4-Methylthiazole (6.51 g) in dry tetrahydrofuran (50 ml) was stirred under an atmosphere of dry nitrogen and cooled to -70° C. and n-butyllithium (2.5M solution in hexane, 29 ml) was added dropwise. After 30 minutes trimethylsilylchloride (7.14 g) was added and the mixture was allowed to warm to room temperature. After 30 minutes the mixture was again cooled to -70° C. and n-butyllithium (2.5M solution in hexane, 29 ml) was added dropwise. After 30 minutes 3-acetyl-2,5-dimethylfuran (10 g) was added dropwise. The mixture was stirred at -70° C. for 1 hour and was then allowed to warm to room temperature. After 30 minutes, aqueous sodium hydrogen carbonate was added and the mixture was extracted with diethylether. The combined extracts were washed, dried and evaporated to give the title compound which was recrystallised from diethylether. M.p. 100.5°-101.5° C.

Workup

  1. temperatureto warm to room temperature
  2. temperatureAfter 30 minutes the mixture was again cooled to -70° C.
  3. temperatureto warm to room temperature
  4. waitAfter 30 minutes
  5. extractionthe mixture was extracted with diethylether
  6. washThe combined extracts were washed
  7. customdried
  8. customevaporated

Sources & evidence

ORD record
ord-01df543a66bb4268b36a7edbe14246e3
Source dataset
uspto-grants-1998_03
DOI
10.6084/m9.figshare.5104873.v1
Patent number
US05731335

Reaction notes

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On this pageParticipantsConditionsProcedureWorkupSources & evidenceReaction notes