Hydrochloric Acid → 4-(3-Thienyl)-3-butenoic acid

HRID 128663

Reaktionsgleichung

Reaktionsgleichung von HRID 128663
[H-].[Na+].[Cl-].[C:4]([CH2:7][CH2:8][P+](C1C=CC=CC=1)(C1C=CC=CC=1)C1C=CC=CC=1)([OH:6])=[O:5].[S:28]1[CH:32]=[CH:31][C:30]([CH:33]=O)=[CH:29]1.Cl>C1COCC1.CS(C)=O.O>[S:28]1[CH:32]=[CH:31][C:30]([CH:33]=[CH:8][CH2:7][C:4]([OH:6])=[O:5])=[CH:29]1

Komponenten

8

Edukt 4

HCID 313Hydrochloric AcidHCID 24758Sodium hydrideHCID 681353-ThiophenecarboxaldehydeHCID 10270534(2-Carboxyethyl)triphenylphosphonium chloride

Produkt 1

HCID 538324824-(3-Thienyl)-3-butenoic acidAusbeute 61,4 %

Reagenzien, Katalysatoren, Lösungsmittel 3

HCID 679Dimethyl SulfoxideLösungsmittelHCID 962WaterLösungsmittelHCID 8028TetrahydrofuranLösungsmittel

Reaktionsbedingungen

Temperatur
-60 °C

Versuchsvorschrift

To a stirring suspension of 1.60 g (67 mmol) of NaH in 20 mL of THF cooled to -60° C. was added a solution of 12.36 g (33 mmol) of (2-carboxyethyl)triphenylphosphonium chloride (28), prepared in the manner described above in Example 28, and 3.75 g (33 mmol) of 3-thiophene carboxaldehyde in 40 mL of dimethylsulfoxide (DMSO)/THF (3:1). The reaction was stirred for 16 hours at -20° C., and then for 6 hours at 0° C. The reaction was then added to cold H2O. The pH was adjusted to 2 with 2 N HCl. The aqueous layer was extracted with 4×200 mL of EtOAc. The organic layer was treated as described above in Example 14 and chromatographed to yield 3.41 g (61%) of 4-(3-thienyl)-3-butenoic acid (29).

Aufarbeitung

  1. customprepared in the manner
  2. waitfor 6 hours at 0° C
  3. extractionThe aqueous layer was extracted with 4×200 mL of EtOAc
  4. additionThe organic layer was treated
  5. customchromatographed

Quellen und Nachweise

ORD-Eintrag
ord-0171a365cd364840ac2aca09f330afb2
Quelldatensatz
uspto-grants-1995_11
Patentnummer
US05464830

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