Vinyl benzoate → Acetate
Reaction equation
[C:1]([O:9]C=C)(=[O:8])[C:2]1C=CC=[CH:4][CH:3]=1>C(OC)(C)(C)C>[CH:1]([O-:9])=[O:8].[C:1]([O-:9])(=[O:8])[CH3:2].[C:1]([O-:9])(=[O:8])[CH2:2][CH2:3][CH3:4]Participants
Reactant 1
Product 3
Reagents, catalysts & solvents 1
Procedure
A mixture consisting of Intermediate B (80 mg, 0.23 mmol), vinyl ester (0.4 ml), tert.-butyl methylether (18 ml), and lipase enzyme (1.0 g) was gently shaken at room temperature. Benzylic formate, acetate, and n-butyrate were prepared from the corresponding vinyl ester donors using SAM I lipase (Amano Pharmaceutical Co.). Benzoylation was achieved with vinyl benzoate in the presence of Lipozym IM 20 (Novo Nordisk), whereas pivalates and isobutyrates were obtained from the corresponding vinyl esters under catalysis of Novozym SP 435 (Novo Nordisk). Tlc analysis indicated after 2-24 hrs complete disappearance of the starting material (Rf 0.45 (3)). The mixture was filtered and then evaporated under high vacuum (< 40° C.) to give the carboxylic acid (R1—CO2H) salts of the respective benzylic monoesters as colourless to light yellow oils.
Sources & evidence
- ORD record
- ord-8988cc4e30c54abdb3a4b3e7e83339ed
- Source dataset
- uspto-grants-2010_12
- Patent number
- US07855230B2
Reaction notes
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