反应详情

温度

110 °C

To a solution of methyl 2-iodophenylacetate (1.00 g, 3.62 mmol, prepared from the corresponding acid according to litt. Tetrahedron 63, 2007, 9979) in toluene (45 mL) was added Tetrakis(triphenylphosphine)palladium (209 mg, 0.0.181 mmol) and allyl tributylstannane (1.35 mL, 4.34 mmol). The resulting solution was heated to 110° C. for 20 h and then cooled down. The solvents were removed in vacuo. The yellow oil was partitioned between acetonitrile (30 mL) and hexane (30 mL) and the acetonitrile layer was washed with hexane (2*30 mL). The acetonitrile was removed in vacuo and the residue was purified by flash chromatography eluting with cyclohexane and ethyl acetate (15/1) to give Methyl 2-allylphenylacetate (colourless oil, 446 mg, 65%). C12H14O2; MW: 190.24; LCMS (method A) RT 1.74 min; ES: 191 (100%, MH+); IR. 2951, 1734 cm−1; 1H NMR (400 MHz, CDCl3) δ 7.14-7.41 (4H, m), 5.99 (1H, m), 5.12 (1H, m), 5.03 (1H, m), 3.73 (3H, s), 3.72 (2H, s), 3.47 (2H, dt) ppm.

1. temperaturecooled down
2. customThe solvents were removed in vacuo
3. customThe yellow oil was partitioned between acetonitrile (30 mL) and hexane (30 mL)
4. washthe acetonitrile layer was washed with hexane (2*30 mL)
5. customThe acetonitrile was removed in vacuo
6. customthe residue was purified by flash chromatography
7. washeluting with cyclohexane and ethyl acetate (15/1)