Tetrahydrofuran → 2-(1,3-Dioxolan-2-yl)-5-[(2-methoxyethoxy)methyl]-1,3-thiazole

HRID 1881879Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 1881879
[O:1]1[CH2:5][CH2:4][O:3][CH:2]1[C:6]1[S:7][C:8]([CH2:11][OH:12])=[CH:9][N:10]=1.Br[CH2:14][CH2:15][O:16][CH3:17].O1CCCC1.[H-].[Na+]>O.CN(C)C(=O)C>[O:3]1[CH2:4][CH2:5][O:1][CH:2]1[C:6]1[S:7][C:8]([CH2:11][O:12][CH2:14][CH2:15][O:16][CH3:17])=[CH:9][N:10]=1

Komponenten

7

Edukt 4

HCID 8028TetrahydrofuranHCID 24758Sodium hydrideHCID 809722-Bromoethyl methyl etherHCID 59331528[2-(1,3-Dioxolan-2-yl)-1,3-thiazol-5-yl]methanol

Produkt 1

HCID 593316232-(1,3-Dioxolan-2-yl)-5-[(2-methoxyethoxy)methyl]-1,3-thiazoleAusbeute 29,9 %

Reagenzien, Katalysatoren, Lösungsmittel 2

HCID 962WaterLösungsmittelHCID 31374DimethylacetamideLösungsmittel

Versuchsvorschrift

To a mixture of [2-(1,3-dioxolan-2-yl)-1,3-thiazol-5-yl]methanol (1.02 g), 1-bromo-2-methoxyethane (1.14 g), tetrahydrofuran (6 mL) and N,N-dimethylacetamide (6 mL) was slowly added sodium hydride (60%, oil, 0.28 g) at 0° C. The reaction mixture was stirred at room temperature overnight, water was added, 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 basic silica gel column chromatography, and the title compound (0.40 g, yield 29%) was obtained as a colorless oil from a fraction eluted with ethyl acetate-hexane (1:3, volume ratio). MS: 246 (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-8c8f1ea78ea841b4b56a27684f7da514
Quelldatensatz
uspto-grants-2012_11
Patentnummer
US08318746B2

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