Pyridine → Trimethylsilyl crotonate

HRID 1246288Notes

Reaction equation

HRID 1246288 reaction equation
N1C=CC=CC=1.[C:7]([OH:12])(=[O:11])/[CH:8]=[CH:9]/[CH3:10].Cl[Si:14]([CH3:17])([CH3:16])[CH3:15]>CCOCC>[CH3:15][Si:14]([O:11][C:7](=[O:12])/[CH:8]=[CH:9]/[CH3:10])([CH3:17])[CH3:16]

Participants

5

Reactant 3

HCID 1049PyridineHCID 6397ChlorotrimethylsilaneHCID 637090Crotonic Acid

Product 1

HCID 5702560Trimethylsilyl crotonateYield 79%

Reagents, catalysts & solvents 1

HCID 3283Diethyl EtherSolvent

Procedure

Pyridine (138 g, 1.74 mol) is added dropwise to a stirred solution of crotonic acid (125 g, 1.45 mol), and chlorotrimethylsilane (189 g 1.74 mol) in ether (1.5 l) at room temperature. The reaction mixture is allowed to stir at room temperature overnight and the precipitate is removed by filtration. The filtrate is concentrated and the residue is distilled under reduced pressure. The product fraction is collected at 58–70° C. (25 mmHg) to give 180 g of the title compound (79%). GC-MS purity is 93.4%, 1HNMR is consistent with the structure.

Workup

  1. customthe precipitate is removed by filtration
  2. concentrationThe filtrate is concentrated
  3. distillationthe residue is distilled under reduced pressure
  4. customThe product fraction is collected at 58–70° C. (25 mmHg)

Sources & evidence

ORD record
ord-0a1609a66b9f4e61b41fe5763184c4d9
Source dataset
uspto-grants-2006_10
Patent number
US07126025B2

Reaction notes

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