Sulfuric Acid → 2-[(E)-2-(3-Butyl-5-methyl-isoxazol-4-yl)-vinyl]-4-methyl-thiazole-5-carboxylic acid methyl ester

HRID 1923607Notes

Reaction equation

HRID 1923607 reaction equation
S(=O)(=O)(O)O.[CH3:6][O:7][C:8]([C:10]1[S:14][C:13]([CH2:15][CH:16]([C:18]2[C:19]([CH2:24][CH2:25][CH2:26][CH3:27])=[N:20][O:21][C:22]=2[CH3:23])O)=[N:12][C:11]=1[CH3:28])=[O:9].[OH-].[Na+]>C(OCC)(=O)C>[CH3:6][O:7][C:8]([C:10]1[S:14][C:13](/[CH:15]=[CH:16]/[C:18]2[C:19]([CH2:24][CH2:25][CH2:26][CH3:27])=[N:20][O:21][C:22]=2[CH3:23])=[N:12][C:11]=1[CH3:28])=[O:9]

Participants

5

Reactant 3

HCID 1118Sulfuric AcidHCID 14798Sodium HydroxideHCID 666436972-[2-(3-Butyl-5-methyl-isoxazol-4-yl)-2-hydroxy-ethyl]-4-methyl-thiazole-5-carboxylic acid methyl ester

Product 1

HCID 666436512-[(E)-2-(3-Butyl-5-methyl-isoxazol-4-yl)-vinyl]-4-methyl-thiazole-5-carboxylic acid methyl esterYield 94.1%

Reagents, catalysts & solvents 1

HCID 8857Ethyl AcetateSolvent

Conditions

Temperature
90 °C

Procedure

Concentrated sulfuric acid (85 mL) was added to 2-[2-(3-butyl-5-methyl-isoxazol-4-yl)-2-hydroxy-ethyl]-4-methyl-thiazole-5-carboxylic acid methyl ester (9.0 g, 26.6 mmol) then the mixture was heated at 90° C. for 2 h. The solution was carefully dropped into 2N sodium hydroxide (1580 mL) and ethyl acetate (100 mL) saturated sodium bicarbonate was added until pH 10 was reached. The reaction mixture was extracted with ethyl acetate then the combined organic extracts were dried, filtered and concentrated, to give the title compound (8.02 g, 94%) as a yellow oil that was used directly without further purification. MS: m/e=321.2 [M+H]+.

Workup

  1. additionwas added until pH 10
  2. extractionThe reaction mixture was extracted with ethyl acetate
  3. customthe combined organic extracts were dried
  4. filtrationfiltered
  5. concentrationconcentrated

Sources & evidence

ORD record
ord-31d7e03547d943c7b4368c20fe4e0c57
Source dataset
uspto-grants-2012_05
Patent number
US08178522B2

Reaction notes

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