Chlorotrimethylsilane → 2-Trimethylsilyl-3-methoxythiophene

HRID 1297166Notes

Reaction equation

HRID 1297166 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-86bcbf6deefb4369a86ca9a47e41a7d3
Source dataset
uspto-grants-2007_07
Patent number
US07250430B2

Reaction notes

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