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

HRID 843649

反応式

HRID 843649 の反応式
[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]

参加物

3

反応物 2

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

生成物 1

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

反応条件

温度
7.5 °C

実験手順

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.

後処理

  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

出典と根拠

ORDレコード
ord-b0dfefad5db54c2394558b73c489908e
出典データセット
uspto-grants-2002_04
特許番号
US06380204B1

関連ノート

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