2,4-Dibromo-thiazole-5-carbaldehyde → 2,4-Dibromothiazole-5-methanol
Reaktionsgleichung
[Br:1][C:2]1[S:3][C:4]([CH:8]=[O:9])=[C:5]([Br:7])[N:6]=1.[BH4-].[Na+]>CO>[Br:1][C:2]1[S:3][C:4]([CH2:8][OH:9])=[C:5]([Br:7])[N:6]=1Komponenten
4
Edukt 2
Produkt 1
Reagenzien, Katalysatoren, Lösungsmittel 1
Versuchsvorschrift
2,4-Dibromo-thiazole-5-carbaldehyde (2.0 g, 7.4 mmol) in methanol (80 mL) was treated with NaBH4 (419 mg, 11.0 mmol). The reaction mixture was stirred at rt overnight, quenched with 10% NaOH, diluted with water and extracted with ethyl acetate (2×). The solvent was removed, and the resulting residue was chromatographed using hexane/ethyl acetate (3:1) to give the title compound (1.84 g, 91%). MS (DCI/NH3) m/z 274 (M)+. 1H NMR (500 MHz, CDCl3) δ ppm 2.11 (s, 1H) 4.78 (s, 2H).
Aufarbeitung
- customquenched with 10% NaOH
- additiondiluted with water
- extractionextracted with ethyl acetate (2×)
- customThe solvent was removed
- customthe resulting residue was chromatographed
Quellen und Nachweise
- ORD-Eintrag
- ord-7ac8d0d874d84bbda6bc028bddfb0286
- Quelldatensatz
- uspto-grants-2010_04
- Patentnummer
- US07704997B1
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