Oxalyl chloride → 3-Methoxy-5-isoxazolecarbonyl chloride

HRID 516442Notes

Reaction equation

HRID 516442 reaction equation
[CH3:1][O:2][C:3]1[CH:7]=[C:6]([C:8]([OH:10])=O)[O:5][N:4]=1.C(Cl)(=O)C([Cl:14])=O>C1COCC1.CN(C=O)C>[CH3:1][O:2][C:3]1[CH:7]=[C:6]([C:8]([Cl:14])=[O:10])[O:5][N:4]=1

Participants

5

Reactant 2

HCID 65578Oxalyl chlorideHCID 3277173-Methoxy-1,2-oxazole-5-carboxylic acid

Product 1

HCID 121963593-Methoxy-5-isoxazolecarbonyl chlorideYield 88.7%

Reagents, catalysts & solvents 2

HCID 6228DimethylformamideCatalystHCID 8028TetrahydrofuranSolvent

Procedure

To a solution of 3-methoxyisoxazole-5-carboxylic acid (420 mg, 3 mmol) in THF (15 mL) and DMF (5 drop) was added dropwise oxalyl chloride (650 μL, 7 mmol) at 0° C. The mixture was then stirred at room temperature for 3 hours. The solution was concentrated in vacuo to yield the title compound as a light yellow oil (430 mg).

Workup

  1. concentrationThe solution was concentrated in vacuo

Sources & evidence

ORD record
ord-a8e8020150a84d619f1c2d94e2ab23d5
Source dataset
uspto-grants-2015_08
Patent number
US09108934B2

Reaction notes

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