反応 #73547

反応方程式

diethyl (2E)-pent-2-enedioate

Et3N

3-bromopyridine

→

diethyl (2Z)-3-(pyridin-3-yl)pent-2-enedioate

収率 87.1%

溶媒

DMF

EtOAc

反応条件

後処理

1. 1
   温度The medium is then heated for 24 hours at 90° C.
2. 2
   洗浄washed with 100 mL of water
3. 3
   乾燥dried over Na2SO4
4. 4
   濃縮concentrated under reduced pressure
5. 5
   その他purified by chromatography on a column of silica gel
6. 6
   洗浄eluting with a cyclohexane/EtOAc gradient of 0 to 10% EtOAc

実験手順

To a solution of 15 mL (85.6 mmol) of diethyl (2E)-pent-2-enedioate in 5 mL of anhydrous DMF are added, under a stream of argon, 0.62 g (2.8 mmol) of Pd(OAc)2, 1.7 g (5.56 mmol) of P(OTol)3 and 5.5 mL (39.7 mmol) of Et3N, the medium is then heated to 40° C. and 4 mL (39.75 mmol) of 3-bromopyridine are added. The medium is then heated for 24 hours at 90° C., and then taken up in 100 mL of EtOAc, washed with 100 mL of water, dried over Na2SO4, concentrated under reduced pressure and purified by chromatography on a column of silica gel, eluting with a cyclohexane/EtOAc gradient of 0 to 10% EtOAc. 9.12 g of diethyl (2Z)-3-(pyridin-3-yl)pent-2-enedioate are obtained in the form of a yellow wax.

出典