Réaction #40886

Équation de réaction

Water

ethyl acetate

2-bromo-1-phenylethanone

→

title compound

Rendement 50.0%

1—Ethyl [2-oxo-3-(2-oxo-2-phenylethyl)cyclohexyl]acetate

Rendement 50.0%

Solvants

dimethylformamide

Conditions de réaction

Traitement

1. 1
   workup.STIRRINGto stir for a further 24 h
2. 2
   Lavagewashed with water
3. 3
   ExtractionThe aqueous fraction was re-extracted three times with ethyl acetate
4. 4
   Lavagethe combined organic fractions washed three times with water
5. 5
   Séchagedried over sodium sulfate
6. 6
   Filtrationfiltered
7. 7
   Concentrationconcentrated in vacuo

Mode opératoire

Intermediate 2 (667 mg, 2.81 mmol) was dissolved in dimethylformamide (14 ml), 2-bromo-1-phenylethanone (560 mg, 2.81 mmol) was added and the reaction stirred for 24 h at room temperature. Water (5 ml) was added and the reaction allowed to stir for a further 24 h. The mixture was then diluted with ethyl acetate (100 ml) and washed with water. The aqueous fraction was re-extracted three times with ethyl acetate and the combined organic fractions washed three times with water, then dried over sodium sulfate, filtered and concentrated in vacuo. Column chromatography (10-20% ethyl acetate/hexanes) provided the title compound as a pale yellow oil (428 mg, 50%).

Source