Hydrochloric Acid → 4-[4-(cyclopropylsulfonyl)phenyl]-5-(tetrahydro-2H-pyran-4-yl)pent-1-en-3-one

HRID 1881815Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 1881815
[CH:1]1([S:4]([C:7]2[CH:12]=[CH:11][C:10]([CH:13]([CH2:20][CH:21]3[CH2:26][CH2:25][O:24][CH2:23][CH2:22]3)[C:14](N(OC)C)=[O:15])=[CH:9][CH:8]=2)(=[O:6])=[O:5])[CH2:3][CH2:2]1.[CH:27]([Mg]Br)=[CH2:28].Cl>O1CCCC1>[CH:1]1([S:4]([C:7]2[CH:12]=[CH:11][C:10]([CH:13]([CH2:20][CH:21]3[CH2:26][CH2:25][O:24][CH2:23][CH2:22]3)[C:14](=[O:15])[CH:27]=[CH2:28])=[CH:9][CH:8]=2)(=[O:5])=[O:6])[CH2:2][CH2:3]1

Komponenten

5

Edukt 3

HCID 313Hydrochloric AcidHCID 593315972-[4-(cyclopropylsulfonyl)phenyl]-N-methoxy-N-methyl-3-(tetrahydro-2H-pyran-4-yl)propanamideHCID 178418507HCID 178418507, Verbindung

Produkt 1

HCID 593312584-[4-(cyclopropylsulfonyl)phenyl]-5-(tetrahydro-2H-pyran-4-yl)pent-1-en-3-oneAusbeute 46 %

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 8028TetrahydrofuranLösungsmittel

Versuchsvorschrift

To a solution of 2-[4-(cyclopropylsulfonyl)phenyl]-N-methoxy-N-methyl-3-(tetrahydro-2H-pyran-4-yl)propanamide (10.2 g) in tetrahydrofuran (100 mL) was added dropwise vinylmagnesium bromide (1.0M tetrahydrofuran solution, 73 mL) under ice-cooling. The reaction mixture was stirred overnight at room temperature, 1M hydrochloric acid (80 mL) was added and the mixture was further stirred for 30 min. The reaction mixture was extracted with ethyl acetate, and the ethyl acetate layer was washed with saturated aqueous sodium hydrogen carbonate and saturated brine, dried (MgSO4) and concentrated. The residue was subjected to silica gel column chromatography, and the title compound (4.25 g, yield 46%) was obtained as colorless crystals from a fraction eluted with ethyl acetate-hexane (1:2, volume ratio). melting point 92-93° C. MS: 349 (MH+).

Aufarbeitung

  1. temperaturecooling
  2. stirringthe mixture was further stirred for 30 min
  3. extractionThe reaction mixture was extracted with ethyl acetate
  4. washthe ethyl acetate layer was washed with saturated aqueous sodium hydrogen carbonate and saturated brine
  5. dry with materialdried (MgSO4)
  6. concentrationconcentrated

Quellen und Nachweise

ORD-Eintrag
ord-b3115777b023494792c5168f2254f2ab
Quelldatensatz
uspto-grants-2012_11
Patentnummer
US08318746B2

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