Formic Acid → ethyl (3R)-2-chloro-3-hydroxy-4-phenylbutyrate

HRID 1173771

Reaktionsgleichung

Reaktionsgleichung von HRID 1173771
[Cl:1][CH:2]([C:8](=[O:16])[CH2:9][C:10]1[CH:15]=[CH:14][CH:13]=[CH:12][CH:11]=1)[C:3]([O:5][CH2:6][CH3:7])=[O:4].CC1C=CC(C(C)C)=CC=1.C(N(CC)CC)C.C(O)=O>ClC1C=CC=CC=1.C(OCC)(=O)C.O>[Cl:1][CH:2]([C@H:8]([OH:16])[CH2:9][C:10]1[CH:11]=[CH:12][CH:13]=[CH:14][CH:15]=1)[C:3]([O:5][CH2:6][CH3:7])=[O:4]

Komponenten

8

Edukt 4

HCID 284Formic AcidHCID 7463P-CymeneHCID 8471TriethylamineHCID 11601176Ethyl 2-chloro-3-oxo-4-phenylbutyrate

Produkt 1

HCID 59203390ethyl (3R)-2-chloro-3-hydroxy-4-phenylbutyrateAusbeute 107,1 %

Reagenzien, Katalysatoren, Lösungsmittel 3

HCID 962WaterLösungsmittelHCID 7964ChlorobenzeneLösungsmittel3×HCID 8857Ethyl AcetateLösungsmittel

Reaktionsbedingungen

Temperatur
40 °C

Versuchsvorschrift

Ethyl 2-chloro-3-oxo-4-phenylbutyrate (180 mg, 0.7 mmol) and RuCl[(S,S)-TsDPEN])p-cymene) complex (10 mg, 2 mol %) were mixed, and the mixture was dissolved in chlorobenzene (1 ml). A chlorobenzene solution (1 ml) of triethylamine (374 mg, 5 equivalents) was added, and then a chlorobenzene solution (1 ml) of formic acid (102 mg, 3 equivalents) was gradually added dropwise. After the mixture was stirred at 40° C. for 3 hours, water (4 ml) was added. Ethyl acetate (10 ml) was added for extraction, and the organic layer was concentrated under reduced pressure to obtain the title compound as a brown oil (182 mg, yield: 100%).

Aufarbeitung

  1. concentrationthe organic layer was concentrated under reduced pressure

Quellen und Nachweise

ORD-Eintrag
ord-0fb06840647044cc93f881a40e5455f8
Quelldatensatz
uspto-grants-2010_11
Patentnummer
US07834190B2

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