Acetone → 2-Bromo-1-thiophen-3-yl-butan-1-one

HRID 2266170

Reaktionsgleichung

Reaktionsgleichung von HRID 2266170
CC[Mg+].[Br-].C[C:6]([OH:9])(C)C.[CH3:10][C:11]([CH3:13])=[O:12].[Br:14][CH:15]([CH2:23][CH3:24])[C:16]([C:18]1[CH:22]=[CH:21][S:20][CH:19]=1)=[O:17]>C1C=CC=CC=1>[Br:14][CH:15]([CH2:23][CH3:24])[C:16]([C:18]1[CH:22]=[CH:21][S:20][CH:19]=1)=[O:17].[S:20]1[CH:21]=[CH:22][C:18]([CH:16]([CH2:15][CH3:23])[C:6](=[O:9])[CH2:10][C:11](=[O:12])[CH3:13])=[CH:19]1

Komponenten

7

Edukt 4

HCID 180Acetone2×HCID 6386tert-ButanolHCID 595986182-Bromo-1-thiophen-3-yl-butan-1-oneHCID 178461630HCID 178461630, Verbindung

Produkt 2

HCID 595986182-Bromo-1-thiophen-3-yl-butan-1-oneHCID 595986385-Thiophen-3-yl-heptane-2,4-dione

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 241BenzeneLösungsmittel2×

Reaktionsbedingungen

Temperatur
0 °C

Versuchsvorschrift

EtMgBr (6.69 ml, 13 mmol, 2 M in ethyl ether) in benzene (10 ml) was cooled to zero degrees C, and tBuOH (1.28 ml, 13 mmol) was slowly added. The reaction mixture was stirred at zero degrees C for 5 minutes, then acetone (530 ul, 7 mmol) was added, followed by a solution of 2-Bromo-1-thiophen-3-yl-butan-1-one (1.3 g, 6 mmol) in 3 ml benzene via cannula. The reaction mixture was heated to reflux for 1 hour, and acetone (250 ul) was added. The reaction mixture was heated 2 hours more at reflux. The reaction was cooled, quenched with 1 N HCl (10 ml), extracted three times with diethyl ether, washed brine, and dried over magnesium sulfate. The solvent was removed in vacuo and the residue chromatographed (5% ethyl acetate/hexanes) to give 247 mg of 2-Bromo-1-thiophen-3-yl-butan-1-one starting material and 520 mg of 5-Thiophen-3-yl-heptane-2,4-dione, 44% .

Aufarbeitung

  1. temperatureThe reaction mixture was heated
  2. temperatureto reflux for 1 hour
  3. temperatureThe reaction mixture was heated 2 hours more
  4. temperatureat reflux
  5. temperatureThe reaction was cooled
  6. customquenched with 1 N HCl (10 ml)
  7. extractionextracted three times with diethyl ether
  8. washwashed brine
  9. dry with materialdried over magnesium sulfate
  10. customThe solvent was removed in vacuo
  11. customthe residue chromatographed (5% ethyl acetate/hexanes)

Quellen und Nachweise

ORD-Eintrag
ord-ccbfb89603834a1a90ac0f1bafeaa854
Quelldatensatz
uspto-grants-2010_12
Patentnummer
US07858632B2

Verknüpfte Notizen

Wird geladen…