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

HRID 1737273Notes

Reaction equation

HRID 1737273 reaction equation
[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]

Participants

3

Reactant 2

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

Product 1

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

Conditions

Temperature
7.5 °C

Procedure

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. The material was used without further purification.

Workup

  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

Sources & evidence

ORD record
ord-83665403f5ef4840950213d52059bbef
Source dataset
uspto-grants-1999_10
Patent number
US05962457

Reaction notes

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