反应详情

To a solution of ethyl 6-chloro-8-iodo-2-(trifluoromethyl)-2H-chromene-3-carboxylate prepared as in U.S. Pat. No. 6,271,253 B1 Example 73, Step 2 (0.342 g, 0.790 mmole) in degassed anhydrous toluene was added Pd(PPh3)4 (54 mg, 0.47 mmole), CuI (15 mg, 0.079 mmole), TEA (0.275 mg, 2.72 mmole) and 2-methylbut-1-en-3-yne (0.247 g, 3.74 mmole) and the mixture was stirred under a N2 atmosphere. After the reaction was determined to be complete by GCMS, H2O and EtOAc were added and the layers were separated. The EtOAc layer was washed with 10% HCl, twice with H2O, twice with aqueous NH4Cl, dried over Na2SO4 and concentrated in vacuo. Purification of the crude product by silica chromatography (95:5 hexanes:EtOAc) gave 155 mg (53% yield) of the product as a white crystalline solid: 1H NMR (CDCl3/300 MHz) 7.62 (s, 1H), 7.37 (d, 1H, J=2.4 Hz), 7.14 (d, 1H, J=2.4 Hz), 5.80 (q, 1H, J=6.6 Hz), 5.44 (m, 1H), 5.35-5.36 (m, 1H), 4.31-4.34 (m, 2H), 1.99 (s, 3H), 1.36 (t, 3H, J=7.1 Hz).

1. additionwere added
2. customthe layers were separated
3. washThe EtOAc layer was washed with 10% HCl, twice with H2O, twice with aqueous NH4Cl
4. dry with materialdried over Na2SO4
5. concentrationconcentrated in vacuo
6. customPurification of the crude product by silica chromatography (95:5 hexanes:EtOAc)