Ethanol → [2-(Thiophen-3-yl)ethyl]propanedioic acid

HRID 962881

Reaktionsgleichung

Reaktionsgleichung von HRID 962881
[OH-:1].[K+].C([C:5]([CH2:16]CC(O)=O)([CH2:9][CH2:10][C:11]1[CH:15]=[CH:14][S:13][CH:12]=1)[C:6]([O-:8])=[O:7])C.C([OH:23])C>O>[C:16]([CH:5]([CH2:9][CH2:10][C:11]1[CH:15]=[CH:14][S:13][CH:12]=1)[C:6]([OH:8])=[O:7])([OH:23])=[O:1]

Komponenten

5

Edukt 3

HCID 702EthanolHCID 14797Potassium HydroxideHCID 86747833Ethyl-2-Carboxyethyl-4-(3-Thienyl)-Butanoate

Produkt 1

HCID 54550536[2-(Thiophen-3-yl)ethyl]propanedioic acid

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 962WaterLösungsmittel

Versuchsvorschrift

To a stirred solution of 1.4 g (24.96 mmol) of potassium hydroxide in 7.0 ml of 50% ethanol in water, was added the above diester (765 mg, 2.83 mmol) prepared in Example 6. The resulting reaction was allowed to stir at room temperature for two hr, followed by overnight reflux. The resulting mixture was poured into ice-10% HCl, followed by three ether extractions. The combined organic layer was dired with Na2SO4 and evaporated to afford a white solid in 90% which was recrystallized from chloroform-hexane to produce colorless needles. Mp, 118°-119° C.; nmr (DMSO/d6, δ rel TMS) 12.60br s, 2H; 7.53-6.80m, 3H; 3.20t, 1H; 2.60t, 2H; 1.99q, 2H. Ir (KBr, ν cm-1) 2900w, 1710s, 1410w, 1260w, 925w, 780s. El. Anal. Calcd. for C9 H10O4S: C, 56.45; H, 5.92; S, 18.83. Found: C, 56.39; H, 5.92; S, 18.67.

Aufarbeitung

  1. customThe resulting reaction
  2. waitfollowed by overnight
  3. temperaturereflux
  4. extractionfollowed by three ether extractions
  5. customevaporated
  6. customto afford a white solid in 90% which
  7. customwas recrystallized from chloroform-hexane
  8. customto produce colorless needles
  9. customMp, 118°-119° C.

Quellen und Nachweise

ORD-Eintrag
ord-0c1273cdfc2f43b087ad69145863aa8e
Quelldatensatz
uspto-grants-1998_06
Patentnummer
US05760169

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