Vinyl benzoate → Acetate

HRID 50597

Reaktionsgleichung

Reaktionsgleichung von HRID 50597
C(N(C(C)C)CCC(C1C=C(CO)C=CC=1O)C1C=CC=CC=1)(C)C.[C:26]([O:34]C=C)(=[O:33])[C:27]1C=CC=[CH:29][CH:28]=1>C(OC)(C)(C)C>[CH:26]([O-:34])=[O:33].[C:26]([O-:34])(=[O:33])[CH3:27].[C:26]([O-:34])(=[O:33])[CH2:27][CH2:28][CH3:29]

Komponenten

6

Versuchsvorschrift

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 9) 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 disappearence 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.

Quellen und Nachweise

ORD-Eintrag
ord-2674450eb3d74b04b9db1d225d794c76
Quelldatensatz
uspto-grants-2004_03
Patentnummer
US06713464B1

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