Piperidine → 3-(3-Fluoro-4-methoxy-phenylsulfanyl)-3-methyl-butyric acid

HRID 619608Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 619608
[CH3:1][C:2]([CH3:7])=[CH:3][C:4]([OH:6])=[O:5].[F:8][C:9]1[CH:10]=[C:11]([SH:17])[CH:12]=[CH:13][C:14]=1[O:15][CH3:16].N1CCCCC1>CCOC(C)=O>[F:8][C:9]1[CH:10]=[C:11]([S:17][C:2]([CH3:7])([CH3:1])[CH2:3][C:4]([OH:6])=[O:5])[CH:12]=[CH:13][C:14]=1[O:15][CH3:16]

Komponenten

5

Edukt 3

HCID 8082PiperidineHCID 109313-Methyl-2-butenoic acidHCID 27590073-Fluoro-4-methoxythiophenol2×

Produkt 1

HCID 218466493-(3-Fluoro-4-methoxy-phenylsulfanyl)-3-methyl-butyric acidAusbeute 101,1 %

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 8857Ethyl AcetateLösungsmittel

Reaktionsbedingungen

Temperatur
105 °C

Versuchsvorschrift

A heavy-walled screw cap tube was charged with 3-methyl-2-butenoic acid (1.23 g, 12.33 mmol), 3-fluoro-4-methoxy thiophenol (Compound 200, 1.95 g, 12.33 mmol), and piperidine (314.8 mg, 3.70 mmol). This mixture was heated to 105° C. for 23 hours, cooled to room temperature and dissolved in EtOAc (100mL). The resulting solution was washed with 1M aqueous HCl, H2O, and saturated aqueous NaCl before being dried over Na2SO4. Concentration of the dry solution under reduced pressure afforded 3.22 g of a clear yellow oil which was used in the next reaction without further purification. 1H NMR (300 MHz, CDCl3) δ: 7.32 (2H, m), 6.94 (1H, t, J=8.4 Hz), 3.92 (3H, s), 2.54 (2H, s), 1.41 (6H, s).

Aufarbeitung

  1. customA heavy-walled screw cap tube
  2. temperaturecooled to room temperature
  3. washThe resulting solution was washed with 1M aqueous HCl, H2O, and saturated aqueous NaCl
  4. dry with materialbefore being dried over Na2SO4

Quellen und Nachweise

ORD-Eintrag
ord-61f98eb6c00e4b1b912fd8b5129f8fd8
Quelldatensatz
uspto-grants-1999_09
Patentnummer
US05958954

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