Triethylamine → Ethyl 4-methyl-3-(pyridin-4-yl)isoxazole-5-carboxylate

HRID 2388195Notes

Reaction equation

HRID 2388195 reaction equation
O[N:2]=[C:3]([C:13]1[CH:18]=[CH:17][N:16]=[CH:15][CH:14]=1)[CH:4]([CH3:12])[C:5](=[O:11])[C:6]([O:8][CH2:9][CH3:10])=[O:7].C(N(CC)CC)C.S(Cl)(C)(=O)=O>C(Cl)Cl.C(=O)(O)[O-].[Na+]>[CH3:12][C:4]1[C:3]([C:13]2[CH:18]=[CH:17][N:16]=[CH:15][CH:14]=2)=[N:2][O:11][C:5]=1[C:6]([O:8][CH2:9][CH3:10])=[O:7]

Participants

6

Reactant 3

HCID 8471TriethylamineHCID 31297Methanesulfonyl chlorideHCID 136341743Ethyl 4-(hydroxyimino)-3-methyl-2-oxo-4-(pyridin-4-yl)butanoate

Product 1

HCID 67530753Ethyl 4-methyl-3-(pyridin-4-yl)isoxazole-5-carboxylateYield 117.4%

Reagents, catalysts & solvents 2

HCID 6344DichloromethaneSolvent2×HCID 516892Sodium BicarbonateSolvent

Procedure

Ethyl 4-(hydroxyimino)-3-methyl-2-oxo-4-(pyridin-4-yl)butanoate (4.68 g, 18.7 mmol) and triethylamine (3.4 mL, 24.3 mmol) were added to 120 mL of CH2Cl2. Mesyl chloride (1.9 mL, 24.3 mmol) was added and the mixture was stirred at room temperature for 20 h. The reaction mixture was diluted with CH2Cl2 and saturated sodium bicarbonate solution was added. The aqueous layer was extracted with additional CH2Cl2 and the combined organic layer was washed with brine and dried over MgSO4. The solvent was removed in vacuo to afford 5.1 g of the title compound. MS: (+) m/z 233.35 (M+1).

Workup

  1. additionwas added
  2. extractionThe aqueous layer was extracted with additional CH2Cl2
  3. washthe combined organic layer was washed with brine
  4. dry with materialdried over MgSO4
  5. customThe solvent was removed in vacuo

Sources & evidence

ORD record
ord-7c056bbdc96d40ccb101012d47146253
Source dataset
uspto-grants-2012_09
Patent number
US08269008B2

Reaction notes

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