3-Benzyloxy-5-isopropyl-N-methoxy-N-methylthiophene-2-carboxamide → (3-Benzyloxy-5-isopropyl-thiophen-2-yl)-(4-methoxy-phenyl)-methanone

HRID 1445334Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 1445334
[CH2:1]([O:8][C:9]1[CH:13]=[C:12]([CH:14]([CH3:16])[CH3:15])[S:11][C:10]=1[C:17](N(OC)C)=[O:18])[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.[CH3:23][O:24][C:25]1[CH:30]=[CH:29][C:28]([Mg]Br)=[CH:27][CH:26]=1>O1CCCC1>[CH2:1]([O:8][C:9]1[CH:13]=[C:12]([CH:14]([CH3:15])[CH3:16])[S:11][C:10]=1[C:17]([C:28]1[CH:29]=[CH:30][C:25]([O:24][CH3:23])=[CH:26][CH:27]=1)=[O:18])[C:2]1[CH:3]=[CH:4][CH:5]=[CH:6][CH:7]=1

Komponenten

4

Edukt 2

HCID 219612223-Benzyloxy-5-isopropyl-N-methoxy-N-methylthiophene-2-carboxamideHCID 178491912HCID 178491912, Verbindung

Produkt 1

HCID 21961226(3-Benzyloxy-5-isopropyl-thiophen-2-yl)-(4-methoxy-phenyl)-methanone

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 8028TetrahydrofuranLösungsmittel2×

Reaktionsbedingungen

Temperatur
22 °C

Versuchsvorschrift

860 mg of 3-benzyloxy-5-isopropyl-N-methoxy-N-methylthiophene-2-carboxamide were dissolved in 50 ml of tetrahydrofuran (THF) and cooled to 0> C. in an ice bath, and 31.3 ml of 0.5 molar 4-methoxyphenymagnesium bromide solution in tetrahydrofuran were added. After 30 min, the ice bath was removed and the reaction mixture was warmed to 22° C. After one hour, 70 ml of saturated sodium bicarbonate solution were added to the reaction mixture, and it was extracted twice with 100 ml of methyl acetate each time. The combined organic phases were washed with 70 ml of saturated sodium chloride solution, dried over sodium sulfate and concentrated. The crude product was purified by column chromatography (SiO2, ethyl acetate/n-heptane=1:3).

Aufarbeitung

  1. temperaturecooled to 0> C
  2. customthe ice bath was removed
  3. waitAfter one hour
  4. addition70 ml of saturated sodium bicarbonate solution were added to the reaction mixture, and it
  5. extractionwas extracted twice with 100 ml of methyl acetate each time
  6. washThe combined organic phases were washed with 70 ml of saturated sodium chloride solution
  7. dry with materialdried over sodium sulfate
  8. concentrationconcentrated
  9. customThe crude product was purified by column chromatography (SiO2, ethyl acetate/n-heptane=1:3)

Quellen und Nachweise

ORD-Eintrag
ord-2c7f5dfa33924f98a20a2d63849e888f
Quelldatensatz
uspto-grants-2010_02
Patentnummer
US07666848B2

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