Ethanol → Ethyl 2-((2-methoxyethoxy)methyl)thiazole-4-carboxylate

반응식

[CH3:1][O:2][CH2:3][CH2:4][O:5][CH2:6][C:7](=[S:9])[NH2:8].C([CH:12](Br)[C:13](=O)[C:14]([O-:16])=[O:15])C.[CH2:19](O)[CH3:20]>>[CH3:1][O:2][CH2:3][CH2:4][O:5][CH2:6][C:7]1[S:9][CH:12]=[C:13]([C:14]([O:16][CH2:19][CH3:20])=[O:15])[N:8]=1

참가 물질

반응물 3

HCID 702Ethanol

HCID 21948992Ethylbromopyruvate

HCID 24694105HCID 24694105, 화합물

생성물 1

HCID 86700891Ethyl 2-((2-methoxyethoxy)methyl)thiazole-4-carboxylate수율 81%

실험 절차

To a solution of 2-(2-methoxyethoxyl)ethanethioamide (Example 6B, 3.26 g, 21.85 mmol) in ethanol (60 mL) was added dropwise ethylbromopyruvate (3.7 mL, 29.5 mmol) and the mixture was refluxed for 18 hours. The reaction was then concentrated under vacuum, diluted with ethyl acetate, washed with water (1×), brine (1×), dried over anhydrous magnesium sulfate, filtered and concentrated. The residue was purified by silica gel column chromatography (3.5×10 cm, 30% ethyl acetate/CH2Cl2) to give the title material (4.36 g, 81%) as an oil. LC (Method F): 1.791 min. 1H NMR (CDCl3, 400 MHz) δ ppm: 8.16 (s, 1H), 4.87 (s, 2H), 4.41 (q, J=7.10 Hz, 2H), 3.74-3.77 (m, 2H), 3.57-3.60 (m, 2H), 3.39 (s, 3H), 1.39 (t, J=7.10 Hz, 3H).