反应详情

Potassium tert-butoxide (40.4 g, 0.36 mol) was added portionwise to a solution of 5-chloro-2-(2-chloroethoxy)benzoate (76 g, 0.3 mol) in 600 mL of THF at 0° C. After stirring at that temperature for 1 hour, TLC showed complete consumption of starting material and the mixture was poured into ice water. The aqueous layer was extracted twice with EtOAc (200 mL), and the combined organics were evaporated to dryness. The residue was purified by silica gel column chromatography (Hexanes/EtOAc=50:1-30:1) to afford 22 g (34%) of methyl 5-chloro-2-(vinyloxy)benzoate. 1H NMR (400 MHz, CDCl3) δ: 7.76 (d, 1H), 7.38 (dd, 1H), 7.00 (d, 1H), 6.52 (dd, 1H), 4.67 (dd, 1H), 4.44 (dd, 1H), 3.83 (s, 3H).

1. customconsumption of starting material
2. additionthe mixture was poured into ice water
3. extractionThe aqueous layer was extracted twice with EtOAc (200 mL)
4. customthe combined organics were evaporated to dryness
5. customThe residue was purified by silica gel column chromatography (Hexanes/EtOAc=50:1-30:1)