反应详情

Methylmagnesium bromide (9.7 ml, 29 mmole) is added to 20 ml dry tetrahydrofuran in an oven dried 100 ml two neck round bottom flask under nitrogen at 0° C. The solution is treated with 4-t-Butyl-2-pyridine-carboxaldehyde (3.8 g, 23.3 mmole) in 2×5 ml diethyl ether followed by 10 ml diethyl ether. The reaction is warmed to room temperature and then to reflux for 1 h. The mixture is cooled to 0° C., is quenched with 1×20 ml 10% hydrochloric acid, and the pH is adjusted to 9 with 2 N sodium hydroxide. The layers are separated, the aqueous layer is extracted with 4×25 ml dichloromethane, and the combined organics are dried over potassium carbonate. The dried organics are concentrated in vacuo to give 3.9 g (93%) of 4-t-Butyl-2-(1-hydroxyethyl)-pyridine as a tan solid. Analytical material is obtained via recrystallization from hexane.

1. dry with materialdried 100 ml two neck round bottom flask under nitrogen at 0° C
2. temperatureto reflux for 1 h
3. temperatureThe mixture is cooled to 0° C.
4. customis quenched with 1×20 ml 10% hydrochloric acid
5. customThe layers are separated
6. extractionthe aqueous layer is extracted with 4×25 ml dichloromethane
7. dry with materialthe combined organics are dried over potassium carbonate
8. concentrationThe dried organics are concentrated in vacuo