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Hydrochloric Acid → 4-[3-chloro-4-(methylsulfonyl)phenyl]-5-[(2R,3R,7R)-2,3-diphenyl-1,4-dioxaspiro[4.4]non-7-yl]pent-1-en-3-one

HRID 1881906
Notizen
Druckvorschau

Reaktionsgleichung

Reaktionsgleichung von HRID 1881906
[Cl:1][C:2]1[CH:3]=[C:4]([CH:12]([CH2:19][C@H:20]2[CH2:40][CH2:39][C:22]3([O:26][C@H:25]([C:27]4[CH:32]=[CH:31][CH:30]=[CH:29][CH:28]=4)[C@@H:24]([C:33]4[CH:38]=[CH:37][CH:36]=[CH:35][CH:34]=4)[O:23]3)[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:41]([Mg]Br)=[CH2:42].Cl>O1CCCC1>[Cl:1][C:2]1[CH:3]=[C:4]([CH:12]([CH2:19][C@H:20]2[CH2:40][CH2:39][C:22]3([O:23][C@H:24]([C:33]4[CH:34]=[CH:35][CH:36]=[CH:37][CH:38]=4)[C@@H:25]([C:27]4[CH:28]=[CH:29][CH:30]=[CH:31][CH:32]=4)[O:26]3)[CH2:21]2)[C:13](=[O:14])[CH:41]=[CH2:42])[CH:5]=[CH:6][C:7]=1[S:8]([CH3:11])(=[O:10])=[O:9]
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Komponenten

5

Edukt 3

HCID 313Hydrochloric AcidHCID 593315872-[3-chloro-4-(methylsulfonyl)phenyl]-3-[(2R,3R,7R)-2,3-diphenyl-1,4-dioxaspiro[4.4]non-7-yl]-N-methoxy-N-methylpropaneamideHCID 178418507HCID 178418507, Verbindung

Produkt 1

HCID 593315944-[3-chloro-4-(methylsulfonyl)phenyl]-5-[(2R,3R,7R)-2,3-diphenyl-1,4-dioxaspiro[4.4]non-7-yl]pent-1-en-3-oneAusbeute 90 %

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 8028TetrahydrofuranLösungsmittel

Versuchsvorschrift

A solution of 2-[3-chloro-4-(methylsulfonyl)phenyl]-3-[(2R,3R,7R)-2,3-diphenyl-1,4-dioxaspiro[4.4]non-7-yl]-N-methoxy-N-methylpropaneamide (3.05 g) in tetrahydrofuran (30 mL) was cooled to 0° C., and vinylmagnesium bromide (1.0M tetrahydrofuran solution, 22.1 mL) was added dropwise. The reaction mixture was stirred at room temperature for 4 hr, and poured into 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 (2.58 g, yield 90%) was obtained as a colorless 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-9e1b35bf90b44ccb9082440303838f02
Quelldatensatz
uspto-grants-2012_11
DOI
10.6084/m9.figshare.5104873.v1
Patentnummer
US08318746B2

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