反应详情

Triphenylphosphine (5.16 g), and imidazole (1.34 g) were dissolved in 3:1 ether:acetonitrile (80 mL), and the reaction was cooled to 0° C. Iodine (5.0 g) was added with vigorous stirring, and the reaction was warmed to ambient temperature. After 1 h, the reaction was recooled to 0° C. and 4-hydroxymethyl-2-(2-methylphenyl)benzoic acid, methyl ester (example 1178C, 4.6 g) was added as a solution in ether (20 mL). After 4 h at ambient temperature, the reaction was diluted with hexane/ether (1:1, 200 mL) and filtered. The filtrate was washed with a dilute solution of Na2SO3 until colorless, then with water (2×50 mL). The organic extracts were washed with brine (20 mL), dried (MgSO4), filtered and concentrated. The residue was purified by silica gel chromatography eluting with 10% EtOAc/hexane to give a light yellow oil (4.7 g) which slowly crystalizes in the freezer. 1H NMR (300 MHz, CDCl3) δ2.06 (s, 3H), 3.60 (s, 3H), 4.45 (ABq, JAB=9.7 Hz, ΔνAB=6.7 Hz, 2H), 7.03 (brd, J=6.6 Hz, 1H), 7.17-7.29 (m, 4H), 7.41 (dd, J=8.1, 1.6 Hz, 1H), 7.90 (d, J=8.1 Hz, 1H)). MS(CI/NH3) m/e: (M+NH4)+ 384.

1. customwas recooled to 0° C.
2. waitAfter 4 h at ambient temperature
3. filtrationfiltered
4. washThe filtrate was washed with a dilute solution of Na2SO3 until colorless, then with water (2×50 mL)
5. washThe organic extracts were washed with brine (20 mL)
6. dry with materialdried (MgSO4)
7. filtrationfiltered
8. concentrationconcentrated
9. customThe residue was purified by silica gel chromatography
10. washeluting with 10% EtOAc/hexane