Réaction #358486

Équation de réaction

hydrochloric acid

product

3-{(E)-2-[4-chlorospiro[bicyclo[4.2.1]non-3-ene-9,2′-[1,3]dioxolan]-3-yl]vinyl}-5-(4-fluorophenyl)-1-methyl-1H-pyrazole

sodium hydrogen carbonate

→

3-chloro-4-{(E)-2-[5-(4-fluorophenyl)-1-methyl-1H-pyrazol-3-yl]vinyl}bicyclo[4.2.1]non-3-en-9-one

Rendement 94.0%

Solvants

THF

Conditions de réaction

Traitement

1. 1
   Extractionextracted with ethyl acetate (3×200 ml)
2. 2
   ExtractionThe organic extract
3. 3
   Lavagewas washed with brine
4. 4
   Séchagedried over MgSO4
5. 5
   Concentrationconcentrated in vacuo
6. 6
   AutreThe residue was purified by flash chromatography
7. 7
   Lavageeluting with ethylacetate: hexane (1:1)

Mode opératoire

A mixture of 2N hydrochloric acid (100 ml) and the product of Step 2 (18.0 g, 43 mmol) in THF (100 ml) was stirred at 60° C. for 2 hrs. The reaction mixture was basified with saturated sodium hydrogen carbonate and then extracted with ethyl acetate (3×200 ml). The organic extract was washed with brine, dried over MgSO4 and concentrated in vacuo. The residue was purified by flash chromatography eluting with ethylacetate: hexane (1:1) to afford 3-chloro-4-{(E)-2-[5-(4-fluorophenyl)-1-methyl-1H-pyrazol-3-yl]vinyl}bicyclo[4.2.1]non-3-en-9-one (14.96 g, 94%). δH (400 MHz, CDCl3) 1.59-1.71 (2H, m), 1.76-1.83 (1H, m), 2.02-2.10 (2H, m), 2.38-2.51 (2H, m), 2.58-2.62 (1H, m), 2.87-2.90 (1H, m), 2.96-3.01 (1H, m), 3.84 (3H, s), 6.49 (1H, s), 6.64 (1H, d, J 16.5), 7.14-7.18 (2H, m), 7.38-7.42 (2H, m), 7.54 (1H, d, J 16.5).

Source