Phenol → Malonate ether

HRID 2188416Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 2188416
C1(O)C=CC=CC=1.[N+](=[C:10]([C:18]([O:20]C(C)(C)C)=[O:19])[C:11]([O:13][C:14](C)(C)[CH3:15])=[O:12])=[N-]>C([O-])(=O)C.[Rh+3].C([O-])(=O)C.C([O-])(=O)C>[C:18]([O-:20])(=[O:19])[CH2:10][C:11]([O-:13])=[O:12].[CH3:10][CH2:11][O:13][CH2:14][CH3:15]

Komponenten

4

Edukt 2

HCID 996PhenolHCID 50146001,3-Di-tert-butyl 2-diazopropanedioate

Produkt 1

HCID 86757830Malonate ether

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 168478Rhodium acetateKatalysator

Versuchsvorschrift

Alkylation of phenol E-4 (from Chart E) is accomplished by a carbenoid insertion reaction with di-t-butyl diazomalonate (Synthesis 1974, 347) catalyzed by rhodium acetate (J. Med. Chem. 1995, 38:4270), affording malonate ether I-1. Removal of the t-butyl esters is accomplished with trifluroacetic acid in methylene chloride, and the benzyl ester is removed by hydrogenolysis, affording the desired triacid I-3.

Quellen und Nachweise

ORD-Eintrag
ord-036e015529674fa7ba2480759bff9883
Quelldatensatz
uspto-grants-2002_06
Patentnummer
US06410585B1

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