Cyclopropyl methyl ketone → 1-[4-Bromo-2-(methylsulphenylmethyl)phenyl]-3-cyclopropylpropan-1,3-dione

HRID 1492384Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 1492384
[CH3:1][C:2]([CH:4]1[CH2:6][CH2:5]1)=[O:3].[Br:7][C:8]1[CH:17]=[CH:16][C:11]([C:12](OC)=[O:13])=[C:10]([CH2:18][S:19][CH3:20])[CH:9]=1.[H-].[Na+].C(=O)(O)[O-].[Na+]>O1CCCC1>[Br:7][C:8]1[CH:17]=[CH:16][C:11]([C:12](=[O:13])[CH2:1][C:2]([CH:4]2[CH2:6][CH2:5]2)=[O:3])=[C:10]([CH2:18][S:19][CH3:20])[CH:9]=1

Komponenten

6

Edukt 4

HCID 13004Cyclopropyl methyl ketoneHCID 24758Sodium hydrideHCID 516892Sodium BicarbonateHCID 18978023Methyl 4-bromo-2-((methylthio)methyl)benzoate

Produkt 1

HCID 189780111-[4-Bromo-2-(methylsulphenylmethyl)phenyl]-3-cyclopropylpropan-1,3-dioneAusbeute 52,1 %

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 8028TetrahydrofuranLösungsmittel2×

Versuchsvorschrift

A solution of cyclopropyl methyl ketone (1.1 g) and methyl 4-bromo-2-(methylsulphenylmethyl)benzoate (3.6 g) in tetrahydrofuran was added to a refluxing suspension of sodium hydride (80%, 0.9 g) in tetrahydrofuran. After the addition was complete, the mixture was maintained at reflux temperature for 30 minutes. It was then cooled and poured onto 100 g of ice and 50 ml of saturated aqueous sodium bicarbonate. The mixture was extracted with hexane, the organic solution dried (anhydrous sodium sulphate) and the solvent evaporated to give 1-[4-bromo-2-(methylsulphenylmethyl)phenyl]-3-cyclopropylpropan-1,3-dione as an orange oil (2.23 g), NMR (CDCl3): 1.00 (2H,m), 1.20 (2H,m), 1.75 (1H,m), 2.03 (3H,s), 3.92 (2H,s), 6.00 (1H,s), 7.35 (1H,m), 7.45 (1H,m), 7.58 (1H,m) 14.74 (1H,s).

Aufarbeitung

  1. additionAfter the addition
  2. temperaturethe mixture was maintained
  3. temperatureat reflux temperature for 30 minutes
  4. temperatureIt was then cooled
  5. extractionThe mixture was extracted with hexane
  6. dry with materialthe organic solution dried (anhydrous sodium sulphate)
  7. customthe solvent evaporated

Quellen und Nachweise

ORD-Eintrag
ord-2b4023733f11430f9ef94dfe6351806e
Quelldatensatz
uspto-grants-1994_12
Patentnummer
US05374606

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