Sodium borohydride → 1-Phenyl-1-[4-(4-pyridyl)-2-thiazolyl]methanol

HRID 4353

Reaktionsgleichung

Reaktionsgleichung von HRID 4353
[C:1]1([C:7]([C:9]2[S:10][CH:11]=[C:12]([C:14]3[CH:19]=[CH:18][N:17]=[CH:16][CH:15]=3)[N:13]=2)=[O:8])[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=1.[BH4-].[Na+]>CO>[C:1]1([CH:7]([C:9]2[S:10][CH:11]=[C:12]([C:14]3[CH:15]=[CH:16][N:17]=[CH:18][CH:19]=3)[N:13]=2)[OH:8])[CH:2]=[CH:3][CH:4]=[CH:5][CH:6]=1

Komponenten

4

Edukt 2

HCID 4311764Sodium borohydrideHCID 140969581-Phenyl-1-[4-(4-pyridyl)-2-thiazolyl]methanone

Produkt 1

HCID 140969591-Phenyl-1-[4-(4-pyridyl)-2-thiazolyl]methanolAusbeute 45 %

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 887MethanolLösungsmittel

Versuchsvorschrift

To a solution of 1-phenyl-1-[4-(4-pyridyl)-2-thiazolyl]methanone (675 g, 0.0025 mol) in methanol (40 mL) was added sodium borohydride (300 mg, 0.0079 mol) in portions and the mixture allowed to stir at room temperature for one hour. The reaction mixture was concentrated, diluted with water, and extracted with ether (3×25 mL). The combined extracts were washed with brine, dried over magnesium sulfate, concentrated, and chromatographed. Recrystallization from hexane/ethyl acetate afforded 1-phenyl-1-[4-(4-pyridyl)-2-thiazolyl]methanol (300 mg, 45%). mp. 146°-147° C.

Aufarbeitung

  1. concentrationThe reaction mixture was concentrated
  2. additiondiluted with water
  3. extractionextracted with ether (3×25 mL)
  4. washThe combined extracts were washed with brine
  5. dry with materialdried over magnesium sulfate
  6. concentrationconcentrated
  7. customchromatographed
  8. customRecrystallization from hexane/ethyl acetate

Quellen und Nachweise

ORD-Eintrag
ord-e29bb60d5a354d0d869838cdbf5e9016
Quelldatensatz
uspto-grants-1988_02
Patentnummer
US04725606

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