Ethyl pyruvate → 2-Trimethylsilanyloxy-acrylic acid ethyl ester

HRID 458122Notes

Reaction equation

HRID 458122 reaction equation
FC(S([O:8][Si:9]([CH3:12])([CH3:11])[CH3:10])(=O)=O)(F)F.[C:13]([O:18][CH2:19][CH3:20])(=[O:17])[C:14]([CH3:16])=O.C(N(C(C)C)CC)(C)C>C(Cl)Cl>[CH2:19]([O:18][C:13](=[O:17])[C:14]([O:8][Si:9]([CH3:12])([CH3:11])[CH3:10])=[CH2:16])[CH3:20]

Participants

5

Reactant 3

HCID 12041Ethyl pyruvateHCID 65367Trimethylsilyl triflateHCID 81531Diisopropylethylamine

Product 1

HCID 111168062-Trimethylsilanyloxy-acrylic acid ethyl esterYield 90%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent2×

Procedure

A solution of trimethylsilyl trifluoromethylsulfonate (9.52 mL, 52.5 mmol) in anhydrous methylene chloride (10 mL) was added to a stirred ice-cooled solution of ethyl pyruvate (5.56 mL, 50 mmol) and diisopropylethyl amine (9.6 mL, 55 mmol) in anhydrous methylene chloride (100 mL) over a period of 15 minutes. The reaction was stirred on ice for 1.5 hours and then at room temperature for 3 hours. The solvent was evaporated at room temperature and the residue treated with anhydrous pentane (200 mL) and cooled in ice. The precipitated solid was filtered off. The filtrate was collected and the pentane evaporated to give 2-trimethylsilanyloxyacrylic acid ethyl ester as a light brown liquid (90% yield). The crude product was used for the next reaction without further purification.

Workup

  1. waitat room temperature for 3 hours
  2. customThe solvent was evaporated at room temperature
  3. additionthe residue treated with anhydrous pentane (200 mL)
  4. temperaturecooled in ice
  5. filtrationThe precipitated solid was filtered off
  6. customThe filtrate was collected
  7. customthe pentane evaporated

Sources & evidence

ORD record
ord-3ebed0d7dec645bb9aba4332e112f22f
Source dataset
uspto-grants-2007_03
Patent number
US07189758B2

Reaction notes

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