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

HRID 1881910Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 1881910
[Cl:1][C:2]1[CH:3]=[C:4]([CH:12]([CH2:19][CH:20]2[CH2:25][CH2:24][O:23][CH2:22][CH2:21]2)[C:13](N(OC)C)=[O:14])[CH:5]=[CH:6][C:7]=1[S:8]([CH3:11])(=[O:10])=[O:9].[CH:26]([Mg]Br)=[CH2:27].Cl>O1CCCC1>[Cl:1][C:2]1[CH:3]=[C:4]([CH:12]([CH2:19][CH:20]2[CH2:21][CH2:22][O:23][CH2:24][CH2:25]2)[C:13](=[O:14])[CH:26]=[CH2:27])[CH:5]=[CH:6][C:7]=1[S:8]([CH3:11])(=[O:9])=[O:10]

Komponenten

5

Edukt 3

HCID 313Hydrochloric AcidHCID 593313932-[3-chloro-4-(methylsulfonyl)phenyl]-N-methoxy-N-methyl-3-(tetrahydro-2H-pyran-4-yl)propanamideHCID 178418507HCID 178418507, Verbindung

Produkt 1

HCID 593312984-[3-chloro-4-(methylsulfonyl)phenyl]-5-(tetrahydro-2H-pyran-4-yl)pent-1-en-3-oneAusbeute 90 %

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 8028TetrahydrofuranLösungsmittel

Versuchsvorschrift

A solution of 2-[3-chloro-4-(methylsulfonyl)phenyl]-N-methoxy-N-methyl-3-(tetrahydro-2H-pyran-4-yl)propanamide (8.64 g) in tetrahydrofuran (90 mL) was cooled to 0° C., and vinylmagnesium bromide (1.0M tetrahydrofuran solution, 88.8 mL) was added dropwise. The reaction mixture was stirred at room temperature for 3 hr, and added to 1M hydrochloric acid, and the mixture was 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 (7.15 g, yield 90%) was obtained as a pale-yellow amorphous solid from a fraction eluted with ethyl acetate-hexane (1:1, volume ratio).

Aufarbeitung

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

Quellen und Nachweise

ORD-Eintrag
ord-9ec3bc3ce3b0471a93008581ecbf6658
Quelldatensatz
uspto-grants-2012_11
Patentnummer
US08318746B2

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