Sodium borohydride → 4-[4-(3-Hydroxyisoindolin-1-on-2-yl)butylthio]pyridine

HRID 6155Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 6155
[C:1]1(=[O:22])[N:5]([CH2:6][CH2:7][CH2:8][CH2:9][S:10][C:11]2[CH:16]=[CH:15][N:14]=[CH:13][CH:12]=2)[C:4](=[O:17])[C:3]2=[CH:18][CH:19]=[CH:20][CH:21]=[C:2]12.[BH4-].[Na+]>C(O)C>[OH:22][CH:1]1[C:2]2[C:3](=[CH:18][CH:19]=[CH:20][CH:21]=2)[C:4](=[O:17])[N:5]1[CH2:6][CH2:7][CH2:8][CH2:9][S:10][C:11]1[CH:16]=[CH:15][N:14]=[CH:13][CH:12]=1

Komponenten

4

Edukt 2

HCID 4311764Sodium borohydrideHCID 14538888HCID 14538888, Verbindung

Produkt 1

HCID 190790764-[4-(3-Hydroxyisoindolin-1-on-2-yl)butylthio]pyridineAusbeute 27,5 %

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 702EthanolLösungsmittel

Versuchsvorschrift

To a solution of 6.25 g (20.0 mol) of 4-(4-phthalimidobutylthio)pyridine in 300 ml of ethanol, 1.51 g (40 mmol) of sodium borohydride was added, and the mixture was stirred at room temperature for 2.5 hours. The solvent was distilled off and saturated saline was added to the residue. The mixture was extracted with chloroform and the extract was dried over anhydrous magnesium sulfate. The solvent was distilled off and the residue was purified by column chromatography (eluent: ethyl acetate) to give 1.73 g of the desired compound (27.5% yield, colorless crystals), mp. 144°-145° C.

Aufarbeitung

  1. distillationThe solvent was distilled off
  2. additionsaturated saline was added to the residue
  3. extractionThe mixture was extracted with chloroform
  4. dry with materialthe extract was dried over anhydrous magnesium sulfate
  5. distillationThe solvent was distilled off
  6. customthe residue was purified by column chromatography (eluent: ethyl acetate)

Quellen und Nachweise

ORD-Eintrag
ord-923c49f34b564c8dbe84a85dc91bb505
Quelldatensatz
uspto-grants-1993_09
Patentnummer
US05246948

Notizen zur Reaktion

Wird geladen…