Water → 2-Oxo-3-carboethoxy-4-(2-bromo-5-methoxyphenyl)butanoic acid, ethyl ester

HRID 5344

Reaktionsgleichung

Reaktionsgleichung von HRID 5344
C[C:2]([CH3:5])([O-:4])C.[K+].[Br:7][C:8]1[CH:13]=[CH:12][C:11]([O:14][CH3:15])=[CH:10][C:9]=1[CH:16]([CH3:20])C([O-])=O.[C:21](OCC)(=[O:27])[C:22]([O:24][CH2:25][CH3:26])=[O:23].O.C[CH2:33][O:34]CC>>[O:27]=[C:21]([CH:20]([C:33]([O:4][CH2:2][CH3:5])=[O:34])[CH2:16][C:9]1[CH:10]=[C:11]([O:14][CH3:15])[CH:12]=[CH:13][C:8]=1[Br:7])[C:22]([O:24][CH2:25][CH3:26])=[O:23]

Komponenten

6

Edukt 5

HCID 962WaterHCID 3283Diethyl Ether2×HCID 7268Diethyl OxalateHCID 23665647Potassium tert-butoxideHCID 1317181192-Bromo-5-methoxyphenyl-propionate

Produkt 1

HCID 156623402-Oxo-3-carboethoxy-4-(2-bromo-5-methoxyphenyl)butanoic acid, ethyl esterAusbeute 90 %

Reaktionsbedingungen

Temperatur
0 °C

Versuchsvorschrift

Potassium t-butoxide (6.72 g) was suspended in 30 ml of anhydrous ether and cooled to 0° C. A solution of 14.35 g of ethyl 3-(2-bromo-5-methoxyphenyl-propionate and 10.95 g diethyl oxalate in 10 ml ether was added dropwise over 15 min. After 2 at 25° C., the reaction was poured into 100 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 17.48 g of the desired product as a colorless oil (90%). NMR (CDCl3) δ1.20 (t, 3H), 1.35 (t, 3H), 3.32 (dd, 2H), 3.76 (s, 3H), 4.18 (q, 2H), 4.32 (q, 2H), 4.53 (t, 1H), 6.67 (dd, 1H), 6.80 (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-29b1539b5e8e4303be8267bfa4999d0d
Quelldatensatz
uspto-grants-1993_09
Patentnummer
US05244888

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