Water → 2-Oxo-3-carboethoxy-5-(2-bromo-5-methoxyphenyl)pentanoic acid ethyl ester

HRID 5353

Reaktionsgleichung

Reaktionsgleichung von HRID 5353
CC(C)([O-])C.[K+].[CH2:7]([O:9][C:10](=[O:23])[CH2:11][CH2:12][CH2:13][C:14]1[CH:19]=[C:18]([O:20][CH3:21])[CH:17]=[CH:16][C:15]=1[Br:22])[CH3:8].[C:24](OCC)(=[O:30])[C:25]([O:27][CH2:28][CH3:29])=[O:26].O>CCOCC>[CH2:28]([O:27][C:25](=[O:26])[C:24](=[O:30])[CH:11]([C:10]([O:9][CH2:7][CH3:8])=[O:23])[CH2:12][CH2:13][C:14]1[CH:19]=[C:18]([O:20][CH3:21])[CH:17]=[CH:16][C:15]=1[Br:22])[CH3:29]

Komponenten

6

Edukt 4

HCID 962WaterHCID 7268Diethyl OxalateHCID 15662398Ethyl 4-(2-bromo-5-methoxy phenyl)butyrateHCID 23665647Potassium tert-butoxide

Produkt 1

HCID 156623992-Oxo-3-carboethoxy-5-(2-bromo-5-methoxyphenyl)pentanoic acid ethyl esterAusbeute 89 %

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 3283Diethyl EtherLösungsmittel2×

Reaktionsbedingungen

Temperatur
0 °C

Versuchsvorschrift

Potassium t-butoxide (26.94 g) was suspended in 130 ml of anhydrous ether and cooled to 0° C. A solution of 60.24 g ethyl -4-(2-bromo-5-methoxy phenyl)butyrate and 43.84 g diethyl oxalate in 60 ml ether was added dropwise over 20 min. After 2 h at 25° C., the reaction was poured into 400 ml H2O and the aqueous layer was separated, acidified to pH 1 and extracted with ether. The ether layer was dried (MgSO4) and the solvent was evaporated to yield 71.26 g of the desired product as a colorless oil (89%). NMR (CDCl3) δ 1.25 (t, 3H), 1.4 (t, 3H), 2.25 (m, 2H), 2.75 (m, 2H), 3.78 (s, 3H), 4.0-4.5 (m, 5H), 6.64 (dd, 1H), 6.79 (d, 1H), 7.40 (d, 1H).

Aufarbeitung

  1. customthe aqueous layer was separated
  2. extractionextracted with ether
  3. dry with materialThe ether layer was dried (MgSO4)
  4. customthe solvent was evaporated

Quellen und Nachweise

ORD-Eintrag
ord-623055db120040d483ebba9a6496e49a
Quelldatensatz
uspto-grants-1993_09
Patentnummer
US05244888

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