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

HRID 843649

반응식

HRID 843649 반응식
[H-].[Al+3].[Li+].[H-].[H-].[H-].[CH3:7][N:8]([CH2:10][C:11]1[S:12][CH:13]=[C:14]([C:16](OCC)=[O:17])[N:15]=1)[CH3:9]>>[CH3:9][N:8]([CH2:10][C:11]1[S:12][CH:13]=[C:14]([CH2:16][OH:17])[N:15]=1)[CH3:7]

참가 물질

3

반응물 2

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

생성물 1

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

반응 조건

온도
7.5 °C

실험 절차

To a mixture of lithium aluminum hydride (4.5 g, 119 mmol) in ice cold tetrahydrofuran (100 mL) was added ethyl 2-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, 1H), 4.71 (s, 2H), 3.73 (s, 2H), 2.50 (br s, 1H), 2.32 (s, 6H). The material was used without further purification.

후처리

  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

출처 및 근거

ORD 기록
ord-b0dfefad5db54c2394558b73c489908e
출처 데이터셋
uspto-grants-2002_04
특허 번호
US06380204B1

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