Chlorotrimethylsilane → 2-Trimethylsilyl-3-methoxythiophene

HRID 6961

Reaction equation

HRID 6961 reaction equation
[Li]CCCC.[CH3:6][O: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[O:7][CH3:6]

Participants

5

Reactant 3

HCID 6397ChlorotrimethylsilaneHCID 1402493-MethoxythiopheneHCID 178418339Butyllithium

Product 1

HCID 110086402-Trimethylsilyl-3-methoxythiopheneYield 82%

Reagents, catalysts & solvents 1

HCID 3283Diethyl EtherSolvent

Conditions

Temperature
-70 °C

Procedure

A solution of n-BuLi (19.7 mL of 1.6 M in hexanes, 31.5 mmol) is added dropwise to a solution of 3-methoxythiophene (3.0 g, 26.3 mmol) in anhydrous Et2O (20 mL) under nitrogen at −70° C. The mixture is stirred at −70° C. for 2 hr. Chlorotrimethylsilane (4.5 mL, 35.4 mmol) is added slowly to the solution. The mixture is warmed to room temperature and stirred for 3 hr. The reaction is quenched with water (50 mL) and hexanes (100 mL). The aqueous layer is extracted with hexanes (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 (4.0 g, 82%) 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 hexanes (100 mL)
  4. extractionThe aqueous layer is extracted with hexanes (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-565e2ecce6004964ad51bb958a449fdc
Source dataset
uspto-grants-2006_08
Patent number
US07084170B2

Linked notes

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