Ethyl 2-((dimethylamino)methyl)thiazole-4-carboxylate → (2-((Dimethylamino)methyl)thiazol-4-yl)methanol

HRID 381273

Reaktionsgleichung

Reaktionsgleichung von HRID 381273
[H-].[Al+3].[Li+].[H-].[H-].[H-].C([O:9][C:10]([C:12]1[N:13]=[C:14]([CH2:17][N:18]([CH3:20])[CH3:19])[S:15][CH:16]=1)=O)C>>[CH3:20][N:18]([CH2:17][C:14]1[S:15][CH:16]=[C:12]([CH2:10][OH:9])[N:13]=1)[CH3:19]

Komponenten

3

Edukt 2

HCID 2039211Ethyl 2-((dimethylamino)methyl)thiazole-4-carboxylateHCID 21226445Aluminium lithium hydride

Produkt 1

HCID 1838020(2-((Dimethylamino)methyl)thiazol-4-yl)methanolAusbeute 62 %

Reaktionsbedingungen

Temperatur
7.5 °C

Versuchsvorschrift

To a mixture of lithium aluminum hydride (4.5 g, 119 mmol) in ice cold tetrahydrofuran (100 mL) was added ethyl2-dimethylaminomethylthiazole-4-carboxylate (8.5 g, 39.7 mmol in 40 mL of tetrahydrofuran) dropwise over 40 min maintaining an internal temperature of 5-10° C. The mixture was stirred at this temperature range for 90 min. The reaction was carefully quenched with saturated aqueous ammonium chloride (30 mL). The resulting gray slurry was stirred 15 min and filtered through celite. The pad was well washed with ethyl acetate. The filtrate was washed with brine and dried over sodium sulfate. Concentration of this organic solution gave 4.2 g (62%) of 2-dimethylaminomethyl-4-hydroxymethylthiazole as an amber oil which had NMR δ 7.12 (s, 1 H), 4.71 (s, 2 H), 3.73 (s, 2 H), 2.50 (br s, 1 H), 2.32 (s, 6 H). The material was used without further purification.

Aufarbeitung

  1. customThe reaction was carefully quenched with saturated aqueous ammonium chloride (30 mL)
  2. stirringThe resulting gray slurry was stirred 15 min
  3. filtrationfiltered through celite
  4. washThe pad was well washed with ethyl acetate
  5. washThe filtrate was washed with brine
  6. dry with materialdried over sodium sulfate

Quellen und Nachweise

ORD-Eintrag
ord-7dc3932d869e4baf9c763bdea79f81d1
Quelldatensatz
uspto-grants-2001_10
Patentnummer
US06306864B1

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