反应详情

A solution of 4.00 g (25.4 mmol) of 2-amino-3-chlorobenzyl alcohol in 30 ml of dry THF was cooled to -78° C., treated with 16.7 ml (26.7 mmol) of 1.60M n-butyllithium in hexane, warmed to 0°-5° C., treated with 3.61 g (25.4 mmol) of methyl iodide and heated at reflux for 5.5 hours. The solvent was removed by evaporation at reduced pressure. The residue was partitioned between 175 ml of ether and water, and the organic phase was separated and dried (MgSO4). The solvent was removed by evaporation at reduced pressure, and the residue was purified by HPLC eluting with EtOAc and hexane (5:95, v/v) to afford 1.1 g of the desired product as a pale brown oil. IR and 1H NMR spectra were in agreement with the assigned structure.

1. temperaturewarmed to 0°-5° C.
2. temperatureheated
3. temperatureat reflux for 5.5 hours
4. customThe solvent was removed by evaporation at reduced pressure
5. customThe residue was partitioned between 175 ml of ether and water
6. customthe organic phase was separated
7. dry with materialdried (MgSO4)
8. customThe solvent was removed by evaporation at reduced pressure
9. customthe residue was purified by HPLC
10. washeluting with EtOAc and hexane (5:95