Reaction #2254179

Reaction equation

HCl

5-[1,3]dioxolan-2-yl-3-methyl-thiophene-2-carboxylic acid (2,2,2-trifluoro-ethyl)-amide

→

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

Yield 51.2%

Solvents

acetone

Conditions

Workup

1. 1
   Otherone night at room temperature, the 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
5. 5
   OtherThe crude product is purified on a semi-preparative HPLC

Procedure

HCl (2N, 4 ml) is added to a solution of 5-[1,3]dioxolan-2-yl-3-methyl-thiophene-2-carboxylic acid (2,2,2-trifluoro-ethyl)-amide (450 mg) in acetone (10 ml). After 4 hours at 50° C. and one night 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. The crude product is purified on a semi-preparative HPLC to yield 5-formyl-3-methyl-thiophene-2-carboxylic acid (2,2,2-trifluoro-ethyl)-amide (196 mg) as a yellowish oil. MS (HPLC/MS): 252 (MH+). Retention time: 2.54 min.

Source