HCID 22258805, Verbindung → HCID 22258798, Verbindung

HRID 1767318Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 1767318
[CH2:1]([O:8][C:9]1[CH:13]=[CH:12][S:11][C:10]=1[C:14](N(OC)C)=[O:15])[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.[CH3:20][Mg]Br>C1COCC1>[CH2:1]([O:8][C:9]1[CH:13]=[CH:12][S:11][C:10]=1[C:14](=[O:15])[CH3:20])[C:2]1[CH:3]=[CH:4][CH:5]=[CH:6][CH:7]=1

Komponenten

4

Edukt 2

HCID 22258805HCID 22258805, VerbindungHCID 178418573HCID 178418573, Verbindung

Produkt 1

HCID 22258798HCID 22258798, VerbindungAusbeute 89 %

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 8028TetrahydrofuranLösungsmittel2×

Reaktionsbedingungen

Temperatur
0 °C

Versuchsvorschrift

To a cold (0° C.) solution of 3-(benzyloxy)-N-methoxy-N-methyl-2-thiophene-carboxamide (3.47 g, 12.50 mmol) in THF (50 mL) was added a solution of methyl-magnesium bromide in THF (1 M, 35 mL). After being stirred at 0° C. for 1 hr, the reaction mixture was quenched with saturated aqueous NH4Cl solution, diluted with water, and extracted with ethyl acetate. The separated organic phase was washed with brine, dried over Na2SO4, filtered and evaporated. The residue was purified by column chromatography on silica gel (hexane/ethyl acetate/CH2Cl2=3/1/1) followed by recrystallization from n-hexane/ethyl acetate to give 1-[3-(benzyloxy)-2-thienyl]ethanone as a white solid (2.592 g, yield; 89%).

Aufarbeitung

  1. customthe reaction mixture was quenched with saturated aqueous NH4Cl solution
  2. additiondiluted with water
  3. extractionextracted with ethyl acetate
  4. washThe separated organic phase was washed with brine
  5. dry with materialdried over Na2SO4
  6. filtrationfiltered
  7. customevaporated
  8. customThe residue was purified by column chromatography on silica gel (hexane/ethyl acetate/CH2Cl2=3/1/1)
  9. customfollowed by recrystallization from n-hexane/ethyl acetate

Quellen und Nachweise

ORD-Eintrag
ord-b282b01a68d04c27ada10492acc95ec3
Quelldatensatz
uspto-grants-2007_06
Patentnummer
US07232909B2

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