p-Toluenesulfonic acid → 1-[4-Chloro-2-(methanesulfonyl)phenyl]-3-cyclopropylpropane-1,3-dione

HRID 343004Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 343004
[Cl:1][C:2]1[CH:22]=[CH:21][C:5]([C:6]([CH:8]([C:16]([CH:18]2[CH2:20][CH2:19]2)=[O:17])C(OC(C)(C)C)=O)=[O:7])=[C:4]([S:23]([CH3:26])(=[O:25])=[O:24])[CH:3]=1.C1(C)C=CC(S(O)(=O)=O)=CC=1>C1(C)C=CC=CC=1>[Cl:1][C:2]1[CH:22]=[CH:21][C:5]([C:6](=[O:7])[CH2:8][C:16]([CH:18]2[CH2:19][CH2:20]2)=[O:17])=[C:4]([S:23]([CH3:26])(=[O:25])=[O:24])[CH:3]=1

Komponenten

4

Edukt 2

HCID 6101p-Toluenesulfonic acidHCID 53638759HCID 53638759, Verbindung

Produkt 1

HCID 545513651-[4-Chloro-2-(methanesulfonyl)phenyl]-3-cyclopropylpropane-1,3-dioneAusbeute 99,6 %

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 1140TolueneLösungsmittel

Versuchsvorschrift

A mixture of t-butyl 2-(4-chloro-2-methylsulphonylbenzoyl)-3-cyclopropyl-3-oxopropionate (9.5 g) and 4-toluenesulphonic acid (15 g) in toluene was stirred and heated at reflux for 3 hours. After cooling, the mixture was washed with water, dried (anhydrous magnesium sulphate) and filtered. The filtrate was evaporated to dryness to give 1-(4-chloro-2-methylsulphonylphenyl)-3-cyclopropylpropan-1,3-dione, (7.1 g) as an orange gum, NMR (CDCl3): 0.8-1.2 (m, 4H), 1.5-1.9 (m,1H), 3.3 (s, 3H), 5.8 (s,1H), 7.3-7.6 (m,2H), 7.9 (s,1H).

Aufarbeitung

  1. temperatureheated
  2. temperatureat reflux for 3 hours
  3. temperatureAfter cooling
  4. washthe mixture was washed with water
  5. dry with materialdried (anhydrous magnesium sulphate)
  6. filtrationfiltered
  7. customThe filtrate was evaporated to dryness

Quellen und Nachweise

ORD-Eintrag
ord-8866f8ac44cf4c30b372e3605cad4b40
Quelldatensatz
uspto-grants-1999_01
Patentnummer
US05859283

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