反应详情

温度

-15 °C

To a solution of sodium hydride (1.2 g of a 60% mineral oil dispersion, 52 mmol) in 25 mL of THF at 0° C., is added 2-hydroxy-5-iodo-benzaldehyde (7.0 g, 28 mmol). To the resulting solution is added 2-methoxy-ethoxymethoxy chloride (3.4 mL, 30 mmol) and 4 mL of 1,3-dimethyl-3,4,5,6-tetrahydro-2(1H)-pyrimidinone. The solution is allowed to warm to ambient temperatures. After 45 minutes, the solution is cooled to -15° C. and 6 mL of a 2 M solution of sodium borohydride in THF is added. The solution is stirred for 10 minutes. After this time, 24 mL of a 2M HCl solution in water is added. The resulting solution is diluted with ether, washed with water and saturated NaCl. The organic layer is dried over MgSO4, filtered and concentrated. The resulting crude material is purified by column chromatography eluting with 40% EtOAc/hexanes to give the title compound (7.6 g, 22.5 mmol) as a white solid.

1. temperatureto warm to ambient temperatures
2. washwashed with water and saturated NaCl
3. dry with materialThe organic layer is dried over MgSO4
4. filtrationfiltered
5. concentrationconcentrated
6. customThe resulting crude material is purified by column chromatography
7. washeluting with 40% EtOAc/hexanes