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

HRID 1033256

Reaktionsgleichung

Reaktionsgleichung von HRID 1033256
[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 dried 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, v, cm-1) 2900w, 1710s, 1410w, 1260w, 925w, 780s. El. Anal. Calcd. for C9H10O4S: 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. dry with materialThe combined organic layer was dried with Na2SO4
  6. customevaporated
  7. customto afford a white solid in 90% which
  8. customwas recrystallized from chloroform-hexane
  9. customto produce colorless needles
  10. customMp, 118°-119° C.

Quellen und Nachweise

ORD-Eintrag
ord-5961026fd5094c069e245569e0ff7f8b
Quelldatensatz
uspto-grants-1994_05
Patentnummer
US05310781

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