تفاعل #2254231

معادلة التفاعل

ammonium chloride

vinylmagnesium bromide

2-dibutoxymethyl-4-fluoro-1-nitro-benzene

vinylmagnesium bromide

→

desired compound

المردود 56.1%

5-Fluoro-1H-indole-7-carbaldehyde

المردود 56.1%

المذيبات

tetrahydrofuran

ظروف التفاعل

المعالجة

1. 1
   درجة الحرارةWarm the reaction mixture −45° C. to −50° C. for 30 minutes
2. 2
   درجة الحرارةWarm the reaction mixture to −45° C. to −50° C. for 20 minutes
3. 3
   درجة الحرارةWarm the mixture to room temperature
4. 4
   استخلاصextract with diethyl ether (200 mL×2)
5. 5
   غسيلWash the combined organic phases with saturated aqueous sodium chloride (400 mL×2)
6. 6
   تجفيفdry over sodium sulfate
7. 7
   تركيزconcentrate under reduced pressure
8. 8
   workup.DISSOLUTIONDissolve the residue in tetrahydrofuran (100 mL)
9. 9
   workup.ADDITIONadd 0.5 N HCl (10 mL)
10. 10
    workup.ADDITIONDilute the mixture with diethyl ether (200 mL)
11. 11
    غسيلwash sequentially with saturated aqueous sodium bicarbonate (200 mL×3) and saturated aqueous sodium chloride (200 mL×2)
12. 12
    تجفيفDry the organic phase over sodium sulfate
13. 13
    تركيزconcentrate under reduced pressure
14. 14
    غسيلeluting with 5% to 10% ethyl acetate in hexanes

الإجراء التجريبي

Add vinylmagnesium bromide (1 M in tetrahydrofuran, 85.2 mL, 85.2 mmol) dropwise to a solution of 2-dibutoxymethyl-4-fluoro-1-nitro-benzene (8.5 g, 28.4 mmol) in tetrahydrofuran (250 mL) at −78° C. Warm the reaction mixture −45° C. to −50° C. for 30 minutes, cool to −78° C., and add vinylmagnesium bromide (1 M in tetrahydrofuran, 85.2 mL, 85.2 mmol) drop wise. Warm the reaction mixture to −45° C. to −50° C. for 20 minutes, then add saturated aqueous ammonium chloride (300 mL). Warm the mixture to room temperature and extract with diethyl ether (200 mL×2). Wash the combined organic phases with saturated aqueous sodium chloride (400 mL×2), dry over sodium sulfate, and concentrate under reduced pressure. Dissolve the residue in tetrahydrofuran (100 mL), add 0.5 N HCl (10 mL), and stir for 20 minutes. Dilute the mixture with diethyl ether (200 mL), wash sequentially with saturated aqueous sodium bicarbonate (200 mL×3) and saturated aqueous sodium chloride (200 mL×2). Dry the organic phase over sodium sulfate and concentrate under reduced pressure. Subject the residue to silica gel chromatography, eluting with 5% to 10% ethyl acetate in hexanes to provide the desired compound as a pale yellow solid (2.6 g, 56%).

المصدر