Chlorotrimethylsilane → 2-Trimethylsilyl-3-methylsulfanylthiophene

HRID 6964Notes

Reaction equation

HRID 6964 reaction equation
[Li]CCCC.[CH3:6][S:7][C:8]1[CH:12]=[CH:11][S:10][CH:9]=1.Cl[Si:14]([CH3:17])([CH3:16])[CH3:15]>CCOCC>[CH3:15][Si:14]([CH3:17])([CH3:16])[C:9]1[S:10][CH:11]=[CH:12][C:8]=1[S:7][CH3:6]

Participants

5

Reactant 3

HCID 6397ChlorotrimethylsilaneHCID 5198063-(Methylthio)thiopheneHCID 178418339Butyllithium

Product 1

HCID 220194692-Trimethylsilyl-3-methylsulfanylthiopheneYield 48%

Reagents, catalysts & solvents 1

HCID 3283Diethyl EtherSolvent

Conditions

Temperature
-70 °C

Procedure

A solution of n-BuLi (5.3 mL of 1.6 M in hexanes, 8.5 mmol) is added dropwise to a solution of 3-methylsulfanylthiophene (1.0 g, 7.7 mmol) in anhydrous Et2O (8 mL) under nitrogen at −70° C. The mixture is stirred at −70° C. for 2 hr. Chlorotrimethylsilane (1.5 mL) is added slowly to the reaction mixture. The mixture is warmed to room temperature and stirred for 3 hr. The reaction is quenched with water (50 mL) and Et2O (50 mL). The aqueous layer is extracted with Et2O (50 mL). The combined organic extracts are dried (Na2SO4), filtered and concentrated. The crude product is chromatographed on silica gel, eluting with hexanes to afford the title compound (0.75 g, 48%) as a colorless liquid.

Workup

  1. temperatureThe mixture is warmed to room temperature
  2. stirringstirred for 3 hr
  3. customThe reaction is quenched with water (50 mL) and Et2O (50 mL)
  4. extractionThe aqueous layer is extracted with Et2O (50 mL)
  5. dry with materialThe combined organic extracts are dried (Na2SO4)
  6. filtrationfiltered
  7. concentrationconcentrated
  8. customThe crude product is chromatographed on silica gel
  9. washeluting with hexanes

Sources & evidence

ORD record
ord-9191d766b42f4cd196abeaea614de401
Source dataset
uspto-grants-2006_08
Patent number
US07084170B2

Reaction notes

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