反应详情

温度

0 °C

3-Acetyl-isoquinoline (1.53 g, 8.9 mmole) is dissolved in 42 ml methanol in a 100 ml one neck round bottom flask at 0° C. The solution is treated portionwise with sodium borohydride (388 mg, 10.3 mmole) and the reaction mixture is stirred 30 min at 0° C. The volatiles are removed in vacuo and the residue is partitioned between 1×100 ml 1N sodium hydroxide and 3×25 ml dichloromethane. The combined organics are dried over potassium carbonate and are concentrated in vacuo to a pale yellow solid. The crude material is chromatographed over 60 g silica gel (230-400 mesh), eluting with 40% acetone/hexane, while collecting 9 ml fractions. Fractions 26-45 are combined and concentrated to afford 1.23 g (80%) of 3-(1-hydroxyethyl)-isoquinoline.

1. customThe volatiles are removed in vacuo
2. customthe residue is partitioned between 1×100 ml 1N sodium hydroxide and 3×25 ml dichloromethane
3. dry with materialThe combined organics are dried over potassium carbonate
4. concentrationare concentrated in vacuo to a pale yellow solid
5. customThe crude material is chromatographed over 60 g silica gel (230-400 mesh)
6. washeluting with 40% acetone/hexane
7. customwhile collecting 9 ml fractions
8. concentrationconcentrated