反応 #44062

反応方程式

NaOH

Pyrazole

Cs2CO3

trans-1,2-cyclohexanediamine

dodecane

3-bromophenylacetic acid

→

title compound

収率 65.0%

[3-(1H-Pyrazol-1-yl)phenyl]acetic acid

収率 65.0%

溶媒

dioxane

反応条件

後処理

1. 1
   その他The mixture was irradiated in a microwave reactor (PersonalChemistry Emrys™ Optimiser, 300 W, 160° C., 20 min)
2. 2
   抽出extracted with Et2O
3. 3
   抽出extracted with ethyl acetate
4. 4
   洗浄this phase was washed with brine
5. 5
   乾燥dried over Na2SO4
6. 6
   その他the solvent was removed under reduced pressure
7. 7
   その他The crude material was purified on SPE cartridge (Silica)
8. 8
   洗浄eluting with a gradient from Cyclohexane/ethyl acetate 8:2, to Cyclohexane/ethyl acetate 1:1

実験手順

Pyrazole (1.2 eq), Cs2CO3 (2.5 eq), CuI (0.5 eq), trans-1,2-cyclohexanediamine (0.6 eq) and dodecane (1 eq), were added to a stirred solution of 3-bromophenylacetic acid (1 eq) in dioxane at room temperature under an inert atmosphere. The mixture was irradiated in a microwave reactor (PersonalChemistry Emrys™ Optimiser, 300 W, 160° C., 20 min), then added to a 1N aqueous solution of NaOH, and extracted with Et2O. The aqueous phase was acidified to pH=3 with HCl 2N, then extracted with ethyl acetate; this phase was washed with brine, dried over Na2SO4 and the solvent was removed under reduced pressure. The crude material was purified on SPE cartridge (Silica) eluting with a gradient from Cyclohexane/ethyl acetate 8:2, to Cyclohexane/ethyl acetate 1:1, affording the title compound in 65% yield.

出典