Reaction #2254180

Reaction equation

Sodium acetate

hydroxylamine hydrochloride

5-formyl-3-methyl-thiophene-2-carboxylic acid (2,2,2-trifluoro-ethyl)-amide

→

5-(hydroxyimino-methyl)-3-methyl-thiophene-2-carboxylic acid (2,2,2-trifluoro-ethyl)-amide

Solvents

THF

water

DMSO

Conditions

Workup

1. 1
   Otherthe reaction is quenched with water
2. 2
   ExtractionThe reaction mixture is extracted three times with ethyl acetate
3. 3
   DryingThe combined organic phases are dried over Na2SO4
4. 4
   Concentrationconcentrated in vacuo

Procedure

Sodium acetate (90 mg) is added to a solution of hydroxylamine hydrochloride (60 mg) and 5-formyl-3-methyl-thiophene-2-carboxylic acid (2,2,2-trifluoro-ethyl)-amide (190 mg) in THF (5 ml), water (1 ml) and DMSO (1 ml). After 3 hours at room temperature, the reaction is quenched with water. The reaction mixture is extracted three times with ethyl acetate. The combined organic phases are dried over Na2SO4 and concentrated in vacuo to yield 5-(hydroxyimino-methyl)-3-methyl-thiophene-2-carboxylic acid (2,2,2-trifluoro-ethyl)-amide. The crude product obtained (206 mg, yellowish oil) is used without further purification. MS (HPLC/MS): 267 (MH+). Retention time: 2.56 min and 2.64 min (two diastereoisomers).

Source