Water → [2-(1,3-Dioxolan-2-yl)-1,3-thiazol-5-yl]methanol

HRID 1881878Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 1881878
[O:1]1[CH2:5][CH2:4][O:3][CH:2]1[C:6]1[S:7][C:8]([CH:11]=[O:12])=[CH:9][N:10]=1.[BH4-].[Na+].O>CO>[O:3]1[CH2:4][CH2:5][O:1][CH:2]1[C:6]1[S:7][C:8]([CH2:11][OH:12])=[CH:9][N:10]=1

Komponenten

5

Edukt 3

HCID 962WaterHCID 4311764Sodium borohydrideHCID 593313182-(1,3-Dioxolan-2-yl)-1,3-thiazole-5-carbaldehyde

Produkt 1

HCID 59331528[2-(1,3-Dioxolan-2-yl)-1,3-thiazol-5-yl]methanolAusbeute 93,1 %

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 887MethanolLösungsmittel

Reaktionsbedingungen

Temperatur
0 °C

Versuchsvorschrift

To a solution of 2-(1,3-dioxolan-2-yl)-1,3-thiazole-5-carbaldehyde (7.00 g) in methanol (30 mL) was slowly added sodium borohydride (0.53 g) at 0° C., and the mixture was stirred at 0° C. for 30 min. Water was added to the reaction mixture, and the mixture was extracted with ethyl acetate. The ethyl acetate layer was washed with saturated brine, dried (MgSO4) and concentrated. The obtained residue was subjected to silica gel column chromatography, and the title compound (6.59 g, yield 93%) was obtained as a colorless oil from a fraction eluted with ethyl acetate. MS: 188 (MH+).

Aufarbeitung

  1. customat 0° C.
  2. extractionthe mixture was extracted with ethyl acetate
  3. washThe ethyl acetate layer was washed with saturated brine
  4. dry with materialdried (MgSO4)
  5. concentrationconcentrated

Quellen und Nachweise

ORD-Eintrag
ord-82af796e31044b2a98260b425c46b84d
Quelldatensatz
uspto-grants-2012_11
Patentnummer
US08318746B2

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