Ethanol → [4-(1,3-Thiazol-2-yl)phenyl]methanol

HRID 241280Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 241280
[S:1]1[CH:5]=[CH:4][N:3]=[C:2]1[C:6]1[CH:13]=[CH:12][C:9]([CH:10]=[O:11])=[CH:8][CH:7]=1.C(O)C.O1CCCC1.[BH4-].[Na+]>O>[S:1]1[CH:5]=[CH:4][N:3]=[C:2]1[C:6]1[CH:7]=[CH:8][C:9]([CH2:10][OH:11])=[CH:12][CH:13]=1

Komponenten

6

Edukt 4

HCID 702EthanolHCID 8028TetrahydrofuranHCID 4311764Sodium borohydrideHCID 105356554-(1,3-Thiazol-2-yl)benzaldehyde

Produkt 1

HCID 24229487[4-(1,3-Thiazol-2-yl)phenyl]methanolAusbeute 94 %

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 962WaterLösungsmittel

Versuchsvorschrift

To 4-(thiazol-2-yl)benzaldehyde (see JP 2001-519414A) (1.57 g, 8.30 mmol) were added ethanol (20 ml), tetrahydrofuran (0.46 ml), and then sodium borohydride (157 mg, 4.15 mmol), followed by stirring at room temperature for 1.5 hours. After completion of the reaction, water was added to the reaction solution, followed by extraction with ethyl acetate. The separated organic layer was dried over anhydrous sodium sulfate, and then concentrated under reduced pressure. The resulting residue was subjected to silica gel column chromatography (eluent; hexane:ethyl acetate=2:1→1:1 (V/V)), and fractions containing the desired compound were concentrated under reduced pressure to afford the title compound (1.49 g) as a white solid. (Yield: 94%)

Aufarbeitung

  1. additionwas added to the reaction solution
  2. extractionfollowed by extraction with ethyl acetate
  3. dry with materialThe separated organic layer was dried over anhydrous sodium sulfate
  4. concentrationconcentrated under reduced pressure
  5. additioncontaining the desired compound
  6. concentrationwere concentrated under reduced pressure

Quellen und Nachweise

ORD-Eintrag
ord-b825a39c12b4445a9af1a1e77d1f61eb
Quelldatensatz
uspto-grants-2014_02
Patentnummer
US08648097B2

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