反応 #2358589

反応方程式

(R/S) 3-iodo-1-(oxan-2-yl)-1H-pyrazole-4-carbaldehyde

1-ethenyl-4-fluorobenzene

potassium carbonate

→

(E)-3-(4-fluorostyryl)-1-(tetrahydro-2H-pyran-2-yl)-1H-pyrazole-4-carbaldehyde

収率 28.1%

溶媒

N,N-dimethylformamide

反応条件

後処理

1. 1
   温度The reaction was cooled to room temperature
2. 2
   その他then quenched by the addition of 100 mL of water
3. 3
   抽出The resulting mixture was extracted with 3×100 mL of ethyl acetate
4. 4
   洗浄The combined organic layers was washed with 3×100 mL of brine
5. 5
   乾燥dried over anhydrous sodium sulfate
6. 6
   濃縮concentrated under vacuum
7. 7
   その他The residue was purified on a silica gel column
8. 8
   洗浄eluted with 1-15% ethyl acetate in petroleum ether

実験手順

A mixture of (R/S) 3-iodo-1-(oxan-2-yl)-1H-pyrazole-4-carbaldehyde (800 mg, 2.61 mmol, 1.00 equiv), 1-ethenyl-4-fluorobenzene (957 mg, 7.84 mmol, 3.00 equiv), Pd(PPh3)4 (302 mg, 0.26 mmol, 0.10 equiv) and potassium carbonate (1082 mg, 7.83 mmol, 3.00 equiv) in N,N-dimethylformamide (10 mL) was stirred under nitrogen at 100° C. overnight. The reaction was cooled to room temperature then quenched by the addition of 100 mL of water. The resulting mixture was extracted with 3×100 mL of ethyl acetate. The combined organic layers was washed with 3×100 mL of brine, dried over anhydrous sodium sulfate and concentrated under vacuum. The residue was purified on a silica gel column eluted with 1-15% ethyl acetate in petroleum ether to give 220 mg (28%) of (E)-3-(4-fluorostyryl)-1-(tetrahydro-2H-pyran-2-yl)-1H-pyrazole-4-carbaldehyde as a yellow oil. LCMS (method D, ESI): RT=1.49 min, m/z=301.0 [M+H]+.

出典