تفاعل #1446774

معادلة التفاعل

DMPU

4-hydroxy-3-iodo-benzonitrile

NaH

methyl bromo-crotonate

→

title compound

المردود 73.7%

Methyl 4-[4-Cyano-2-Iodo-Phenoxy]-But-2-enoate

المردود 73.7%

المذيبات

THF

THF

ظروف التفاعل

المعالجة

1. 1
   درجة الحرارةTo a cooled
2. 2
   workup.ADDITIONwas added a solution
3. 3
   workup.ADDITIONOn complete addition
4. 4
   أخرىthe cold bath was removed
5. 5
   أخرىreplaced with an oil bath
6. 6
   درجة الحرارةcooled to room temperature
7. 7
   workup.ADDITIONThe mixture was then diluted with ethyl acetate
8. 8
   غسيلwashed sequentially with water and brine
9. 9
   تجفيفdried over MgSO4
10. 10
    تركيزconcentrated
11. 11
    أخرىThe residue was triturated with hexane several times

الإجراء التجريبي

To a cooled (0° C.) suspension of NaH (1.5 g of 60% suspension in mineral oil, 38 mmol) in THF (80 mL) was added a solution comprised of 4-hydroxy-3-iodo-benzonitrile (8.4 g, 34 mmol) (reference example 12), methyl bromo-crotonate (6.65 mL tech. grade, approx. 51 mmol) and DMPU (10 mL) in THF (20 mL). On complete addition, the cold bath was removed and replaced with an oil bath. The reaction mixture was heated to 55° C. and stirred at this temperature for 4.5 hr, cooled to room temperature and acidified with 2M aqueous HCl. The mixture was then diluted with ethyl acetate, washed sequentially with water and brine, dried over MgSO4 and concentrated. The residue was triturated with hexane several times, leaving 8.6 g of the title compound as a solid. 1H NMR (CDCl3) d 3.78 (s, 3H), 4.80 (dd, J=4, 1 Hz, 1H), 6.35 (dt, J=16, 1 Hz, 1H), 6.79 (d, J=8 Hz, 1H), 7.05 (dt, J=16, 4 Hz, 1H), 7.60 (dd, J=8, 1 Hz, 1H), 8.06 (d, J=1 Hz, 1H). MS (EI) m/z 343 (M)+.

المصدر