反应详情

To a solution of 3.0 g. (13.8 mmoles) of 1-ethyl-5-hydroxy-6-allyloxindole (Preparation W2) in 30 ml. of tetrahydrofuran at 0° C. was slowly added 13.8 ml. (13.8 mmoles) of a 1M borane-tetrahydrofuran solution. The reaction was stirred for 30 minutes followed by the addition of 50 ml. of 1N sodium hydroxide solution and 25 ml. of a 30% hydrogen peroxide solution. After stirring the reaction for 5 minutes it was acidified with 25 ml. of 4N hydrochloric acid and extracted with methylene chloride (10×50 ml.). The extracts were combined, dried and concentrated to give the crude product, which was purified by chromatographing on 120 g. of silica gel using 5% methanol-methylene chloride as the eluent to give 1.85 g. (56% yield) of the desired product.

1. customat 0° C.
2. additionfollowed by the addition of 50 ml
3. stirringAfter stirring
4. customthe reaction for 5 minutes it
5. extractionof 4N hydrochloric acid and extracted with methylene chloride (10×50 ml.)
6. customdried
7. concentrationconcentrated
8. customto give the crude product, which
9. customwas purified by chromatographing on 120 g
10. customof silica gel using 5% methanol-methylene chloride as the eluent to give 1.85 g