Reacción #1545432

Ecuación de reacción

Water

4-Methoxy-5-methyl-6-(1-ethyl-5-hydroxypyrazol-4-yl) carbonylthiochroman-1,1-dioxide

bromoacetone

potassium carbonate

→

4-methoxy-5-methyl-6-(5-acetylmethyloxy-1-ethylpyrazol-4-yl) carbonylthiochroman-1,1-dioxide

Rendimiento 63.0%

Disolventes

methyl ethyl ketone

Condiciones de reacción

Tratamiento posterior

1. 1
   Temperaturaunder heat for 3 hours
2. 2
   Extracciónthe reaction mixture was extracted with ethyl acetate
3. 3
   OtroIts organic layer was separated
4. 4
   Secadodried over anhydrous sodium sulfate
5. 5
   workup.DISTILLATIONThen, the solvent was distilled off under reduced pressure
6. 6
   Otrothe resultant oil was purified
7. 7
   Otrowith flush column chromatography (Wako Gel C-300: hexane/ethyl acetate1:2)

Procedimiento

4-Methoxy-5-methyl-6-(1-ethyl-5-hydroxypyrazol-4-yl) carbonylthiochroman-1,1-dioxide was used as a starting material (XIH). And, 0.4 g (1.10 mmol) thereof was dissolved in 10 ml of methyl ethyl ketone, and 0.15 g (1.10 mmol) of bromoacetone as a reaction reagent (XII) and 0.30 g (2.20 mmol) of potassium carbonate as a base were added. The resultant mixture was refluxed under heat for 3 hours. Water was added to the reaction mixture, and the reaction mixture was extracted with ethyl acetate. Its organic layer was separated, and dried over anhydrous sodium sulfate. Then, the solvent was distilled off under reduced pressure, and the resultant oil was purified with flush column chromatography (Wako Gel C-300: hexane/ethyl acetate1:2) to give 0.29 g (yield 63%) of 4-methoxy-5-methyl-6-(5-acetylmethyloxy-1-ethylpyrazol-4-yl) carbonylthiochroman-1,1-dioxide (Compound No. 59) as an end compound which comes under the general formula (XI). Table 20 shows the structures of the starting material (XIH) and the reaction reagent (XII), and the structure and the yield of the end product (XI).

Fuente