Chlorotrimethylsilane → HCID 69303861, compound

HRID 2222460

Reaction equation

HRID 2222460 reaction equation
[S:1]1[CH:5]=[C:4]([C:6]([OH:8])=[O:7])[C:3]([C:9]([OH:11])=[O:10])=[CH:2]1.Cl[Si](C)(C)C.[CH3:17][CH:18]([CH3:21])[CH2:19]O>>[S:1]1[CH:5]=[C:4]([C:6]([O:8][CH2:17][CH:18]([CH3:21])[CH3:19])=[O:7])[C:3]([C:9]([O:11][CH2:2][CH:3]([CH3:9])[CH3:4])=[O:10])=[CH:2]1

Participants

4

Reactant 3

HCID 6397ChlorotrimethylsilaneHCID 6560IsobutanolHCID 255853Thiophene-3,4-dicarboxylic acid

Product 1

HCID 69303861HCID 69303861, compoundYield 95%

Procedure

A mechanically stirred slurry of 5.00 g of thiophene-3,4-dicarboxylic acid (purchased from Aldrich) in 58.2 mL of 2-methyl-1-propanol was treated with 11.0 mL of chlorotrimethylsilane at room temperature. After completion of the addition, the reaction mixture was stirred at room temperature for 1 h, then at 65° C. for one day, quenched with water at 0° C. and extracted with ether. The combined organic phases were washed with saturated water solution of sodium carbonate, brine, dried over magnesium sulfate, filtered, concentrated on a rotary evaporator, and distilled in vacuum to give 7.86 g (95%) of the title compound of 99.6% GC-purity (bp 113° C./1 mm Hg; colorless oil).

Workup

  1. additionAfter completion of the addition
  2. waitat 65° C. for one day
  3. customquenched with water at 0° C.
  4. extractionextracted with ether
  5. washThe combined organic phases were washed with saturated water solution of sodium carbonate, brine
  6. dry with materialdried over magnesium sulfate
  7. filtrationfiltered
  8. concentrationconcentrated on a rotary evaporator
  9. distillationdistilled in vacuum

Sources & evidence

ORD record
ord-a12a840cc6e04d02a7e870b1634136a6
Source dataset
uspto-grants-2008_05
Patent number
US07371802B2

Linked notes

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