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

HRID 1424343Notes

Reaction equation

HRID 1424343 reaction equation
[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

Participants

4

Reactant 3

HCID 702EthanolHCID 21948992EthylbromopyruvateHCID 24694105HCID 24694105, compound

Product 1

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

Procedure

To a solution of 2-(2-methoxyethoxy)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).

Workup

  1. temperaturethe mixture was refluxed for 18 hours
  2. concentrationThe reaction was then concentrated under vacuum
  3. additiondiluted with ethyl acetate
  4. washwashed with water (1×), brine (1×)
  5. dry with materialdried over anhydrous magnesium sulfate
  6. filtrationfiltered
  7. concentrationconcentrated
  8. customThe residue was purified by silica gel column chromatography (3.5×10 cm, 30% ethyl acetate/CH2Cl2)

Sources & evidence

ORD record
ord-2d986f6770f2454d8dbbed7d82240a67
Source dataset
uspto-grants-2015_01
Patent number
US08927688B2

Reaction notes

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