Pyridine → Trimethylsilyl crotonate
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
Product 1
Reagents, catalysts & solvents 1
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
- customthe precipitate is removed by filtration
- concentrationThe filtrate is concentrated
- distillationthe residue is distilled under reduced pressure
- 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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