Ammonium Chloride → HCID 19600247, Verbindung

HRID 611405Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 611405
[O:1]1[C:9]2[CH2:8][CH2:7][N:6]([S:10]([C:13]3[CH:20]=[CH:19][C:16]([CH:17]=[O:18])=[CH:15][CH:14]=3)(=[O:12])=[O:11])[CH2:5][C:4]=2[CH:3]=[CH:2]1.[Cl-].[NH4+]>O1CCCC1.C1([Mg]Br)C=CC=CC=1>[O:1]1[C:9]2[CH2:8][CH2:7][N:6]([S:10]([C:13]3[CH:20]=[CH:19][C:16]([CH:17]([C:13]4[CH:20]=[CH:19][CH:16]=[CH:15][CH:14]=4)[OH:18])=[CH:15][CH:14]=3)(=[O:12])=[O:11])[CH2:5][C:4]=2[CH:3]=[CH:2]1

Komponenten

5

Edukt 2

HCID 25517Ammonium ChlorideHCID 19600233HCID 19600233, Verbindung

Produkt 1

HCID 19600247HCID 19600247, Verbindung

Reagenzien, Katalysatoren, Lösungsmittel 2

HCID 8028TetrahydrofuranLösungsmittel2×HCID 178418255HCID 178418255, VerbindungLösungsmittel

Versuchsvorschrift

To a solution of 0.252 g (0.865 mmol) of 4-(6,7-dihydro-4H-furo[3,2-c]pyridin-5-ylsulfonyl)benzaldehyde in 30 ml of tetrahydrofuran, phenylmagnesium bromide in tetrahydrofuran (prepared from 2.0 g of bromobenzene and 0.31 g of magnesium in 30 ml of tetrahydrofuran) was added at room temperature until the starting material disappeared on TLC. To the reaction mixture, aqueous ammonium chloride was added, followed by stirring and 3 extractions with ethyl acetate. The combined organic layer was dried over anhydrous magnesium sulfate; the solvent was distilled off under reduced pressure. The resulting crude product was purified by silica gel column chromatography (hexane/ethyl acetate=3/1 to 2/1) to yield the desired product.

Aufarbeitung

  1. extraction3 extractions with ethyl acetate
  2. dry with materialThe combined organic layer was dried over anhydrous magnesium sulfate
  3. distillationthe solvent was distilled off under reduced pressure
  4. customThe resulting crude product was purified by silica gel column chromatography (hexane/ethyl acetate=3/1 to 2/1)

Quellen und Nachweise

ORD-Eintrag
ord-614236c1232f4749855a3d2d585fbe8e
Quelldatensatz
uspto-grants-1999_12
Patentnummer
US05998433

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