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Borohydride → Ethyl 4,4,4-trifluoro-3-hydroxybutanoate

HRID 381793
Notizen
Druckvorschau

Reaktionsgleichung

Reaktionsgleichung von HRID 381793
[BH4-].[F:2][C:3]([F:13])([F:12])[C:4](=[O:11])[CH2:5][C:6]([O:8][CH2:9][CH3:10])=[O:7]>[Ru].[Ni].[Pt].CO.O1CCCC1.[Zn].C(O)(=O)C>[F:2][C:3]([F:12])([F:13])[CH:4]([OH:11])[CH2:5][C:6]([O:8][CH2:9][CH3:10])=[O:7]
KomponentenVersuchsvorschriftQuellen und NachweiseNotizen zur Reaktion

Komponenten

9

Edukt 2

HCID 28123BorohydrideHCID 67793Ethyl 4,4,4-trifluoroacetoacetate

Produkt 1

HCID 136210Ethyl 4,4,4-trifluoro-3-hydroxybutanoateAusbeute 78 %

Reagenzien, Katalysatoren, Lösungsmittel 6

HCID 935NickelKatalysator2×HCID 23939PlatinumKatalysator
HCID 23950
Ruthenium
Katalysator
HCID 57475673ZINC acetic acidKatalysator
HCID 887MethanolLösungsmittel
HCID 8028TetrahydrofuranLösungsmittel

Versuchsvorschrift

There are a number of ways of reducing β-ketoesters which have been disclosed. In addition to hydrogenation, reduction with zinc/acetic acid or with borohydride reagents are known. For the hydrogenation reactions reported in the literature, most use ruthenium, nickel, or baker's yeast as catalyst. All use a solvent. F. G. Kathawala et al. in Helvetica Chimica Acta, 69, 803-805 (1986) disclose an example in which 5% platinum on carbon is used as a catalyst for the reduction of various β-ketoesters using methanol as a solvent. T. Fujima et al. in JP 09268146 A2, Oct. 14, 1997 disclose the hydrogenation of ethyl trifluoroacetoacetate using a nickel catalyst in tetrahydrofuran solvent to provide ethyl 4,4,4-trifluoro-3-hydroxybutyrate in 78% yield. N. Sayo et al. in U.S. 4,933,482, Jun. 12, 1990 disclose the hydrogenation of ethyl trifluoroacetoacetate using a ruthenium catalyst in a polar solvent such as an alcohol or tetrahydrofuran to provide ethyl 4,4,4-trifluoro-3-hydroxybutyrate in 95% yield. None of these references disclose or suggest the process of the present invention in which we have discovered that no solvent is necessary for the catalytic hydrogenation.

Quellen und Nachweise

ORD-Eintrag
ord-afaf3dc7c4e54ba599c4a2c1f92ccf09
Quelldatensatz
uspto-grants-2001_10
DOI
10.6084/m9.figshare.5104873.v1
Patentnummer
US06307094B1

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