反应详情

1-Oxiranylmethyl-4-hydroxy-indole: A mixture of 4-benzyloxyindole (223 mg, 1.0 mmol), 2-bromomethyl-oxirane (168 mg, 1.2 mmol) and 60% sodium hydride (60 mg, 1.5 mmol) in 5 mL THF was refluxed overnight. The solution was poured into NaHCO3 saturated solution (20 mL) and extracted with EtOAc. The organic layer was separated, washed with brine and dried over Na2SO4. The solvent was removed in vacuo. The crude material was purified by column chromatography (1:4, hexane:ethyl acetate) to yield 200 mg of 4-benzyloxy-1-oxiranylmethylindole, which was hydrogenated by 5% Pd/C in 20 mL methanol under H2 (50 psi) to yield 70 mg (37%) of the title compound. 1H NMR (CDCl3): 7.10-7.03 (m, 2H), 6.95 (d, J=8.4 Hz, 1H), 6.56 (dd, J=0.9 Hz, J=3.3 Hz, 1H), 6.51 (dd, J=0.9 Hz, J=7.8 Hz, 1H), 4.40-4.34 (m, 1H), 4.17-4.10 (m, 1H), 3.29-3.26 (m, 1H), 2.81-2.78 (m, 1H), 2.46-2.44 (m, 1H).

1. temperaturewas refluxed overnight
2. extractionextracted with EtOAc
3. customThe organic layer was separated
4. washwashed with brine
5. dry with materialdried over Na2SO4
6. customThe solvent was removed in vacuo
7. customThe crude material was purified by column chromatography (1:4, hexane:ethyl acetate)