Piperidine → 3-(4-Methoxyphenylsulfanyl)-4-phenylbutyric acid

HRID 1107113Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 1107113
[C:1]1([CH2:7][CH:8]=[CH:9][C:10]([OH:12])=[O:11])[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=1.[CH3:13][O:14][C:15]1[CH:20]=[CH:19][C:18]([SH:21])=[CH:17][CH:16]=1.N1CCCCC1>>[CH3:13][O:14][C:15]1[CH:20]=[CH:19][C:18]([S:21][CH:8]([CH2:7][C:1]2[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=2)[CH2:9][C:10]([OH:12])=[O:11])=[CH:17][CH:16]=1

Komponenten

4

Edukt 3

HCID 8082PiperidineHCID 127654-MethoxybenzenethiolHCID 534018584-Phenyl-2-butenoic acid

Produkt 1

HCID 106381083-(4-Methoxyphenylsulfanyl)-4-phenylbutyric acidAusbeute 82 %

Reaktionsbedingungen

Temperatur
110 °C

Versuchsvorschrift

A mixture of 2 g (12.53 mmol) of 4-phenylbut-2-enoic acid, 1.8 mL (14.8 mmol) of 4-methoxybenzenethiol, and 0.4 mL (3.7 mmol) of piperidine is heated at 110° C. in a bomb for 18 hours. The reaction is partitioned between ethyl ether and 1N HCl. The organic layer is dried over anhydrous MgSO4 and concentrated in vacuo. Purification by flash silica gel chromatography affords 3.07 g (82%) of 3-(4-methoxyphenylsulfanyl)-4-phenylbutyric acid as a white crystalline solid.

Aufarbeitung

  1. customThe reaction is partitioned between ethyl ether and 1N HCl
  2. dry with materialThe organic layer is dried over anhydrous MgSO4
  3. concentrationconcentrated in vacuo
  4. customPurification by flash silica gel chromatography

Quellen und Nachweise

ORD-Eintrag
ord-46b1720d905f4b3b9480bf6bc7369970
Quelldatensatz
uspto-grants-2000_05
Patentnummer
US06057369

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