تفاعل #1446773

معادلة التفاعل

methyl 4-[4-cyano-2-iodo-phenoxy]-but-2-enoate

→

title compound

المردود 137.4%

Methyl [5-Cyano-2,3-Dihydro-Benzofuran-3-yl]-Acetate

المردود 137.4%

المذيبات

THF Et2O

—

hexanes

ظروف التفاعل

المعالجة

1. 1
   workup.ADDITIONOn complete addition
2. 2
   أخرىthen quenched with 1 M aqueous HCl (20 mL)
3. 3
   workup.ADDITIONThis mixture was diluted with ethyl acetate
4. 4
   غسيلwashed
5. 5
   تجفيفsequentially, with water and brine, dried over MgSO4
6. 6
   تركيزconcentrated
7. 7
   أخرىThe residue was purified by flash chromatography (eluting with 25% ethyl acetate in hexanes)

الإجراء التجريبي

To a cooled (−100° C.) solution of methyl 4-[4-cyano-2-iodo-phenoxy]-but-2-enoate (4.3 g, 12.5 mmol) (reference example 1 a) in THF: Et2O (4:1, 125 mL) was added dropwise n-buLi (5.5 mL, 2.5 M in hexanes). On complete addition, the reaction mixture was stirred for 15 min then quenched with 1 M aqueous HCl (20 mL). This mixture was diluted with ethyl acetate and washed, sequentially, with water and brine, dried over MgSO4 and concentrated. The residue was purified by flash chromatography (eluting with 25% ethyl acetate in hexanes) to give 3.73 g of the title compound. 1H NMR (CDCl3) d 2.63 (dd, 16, 8 Hz, 1H), 2.80 (dd, J=16, 5 Hz, 1H), 3.74 (s, 3H), 3.91 (m, 1H), 4.35 (dd, J=8, 6 Hz, 1H), 4.86 (t, J=8 Hz, 1H), 6.84 (d, J=8 Hz, 1H), 7.47 (m, 2H). MS (EI) m/z 203 (M)+. MS (EI) m/z 217 (M)+.

المصدر