Hydrochloric Acid → Diethyl 5-benzylthio-2-hydroxy-2,4-hexadienedioate

HRID 477312Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 477312
[CH2:1]([S:8][C:9]([C:21]([O:23][CH2:24][CH3:25])=[O:22])=[CH:10][CH:11]=[C:12](N(C)C)[C:13]([O:15][CH2:16][CH3:17])=[O:14])[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.Cl.C([OH:29])C>>[CH2:1]([S:8][C:9]([C:21]([O:23][CH2:24][CH3:25])=[O:22])=[CH:10][CH:11]=[C:12]([OH:29])[C:13]([O:15][CH2:16][CH3:17])=[O:14])[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1

Komponenten

4

Edukt 3

HCID 313Hydrochloric AcidHCID 702EthanolHCID 54057031Diethyl 5-benzylthio-2-dimethylamino-2,4-hexadienedioate

Produkt 1

HCID 54729633Diethyl 5-benzylthio-2-hydroxy-2,4-hexadienedioate

Reaktionsbedingungen

Temperatur
20 °C

Versuchsvorschrift

The procedure is as in Example 2, starting with diethyl 5-benzylthio-2-dimethylamino-2,4-hexadienedioate (10 g) and 1N aqueous hydrochloric acid solution (41.3 cc) in ethanol (41.3 cc). The mixture is heated to boiling for 2 minutes, and then cooled to a temperature in the region of 20° C. After purification by chromatography on a silica column with a mixture of cyclohexane and ethyl acetate (30:70 by volume) as eluent, diethyl 5-benzylthio-2-hydroxy-2,4-hexadienedioate (6.3 g) (m.p. <40° C.) is obtained [Rf=0.6; thin layer chromatography on silica gel; eluent: cyclohexane/ethyl acetate (30:70 by volume)].

Aufarbeitung

  1. temperatureThe mixture is heated
  2. customAfter purification by chromatography on a silica column
  3. additionwith a mixture of cyclohexane and ethyl acetate (30:70 by volume) as eluent

Quellen und Nachweise

ORD-Eintrag
ord-f8205433e7784f979727375e79bdc056
Quelldatensatz
uspto-grants-1989_12
Patentnummer
US04886835

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