Diethyl Ether → 1-(1-Hydroxyethyl)-5,6,7,8-tetrahydroisoquinoline

Methylmagnesium bromide in diethyl ether (9.3 ml, 28 mmole) is dissolved in 10 ml tetrahydrofuran at 0° C. in an oven dried 100 ml two neck round bottom flask under nitrogen. The solution is treated with 5,6,7,8,-Tetrahydroisoquinoline-1-carbaldehyde (3.61 g, 22.4 mmole) followed by 10 ml diethyl ether. The reaction mixture is warmed to room temperature and then to reflux for 1 h. The mixture is cooled, is quenched with 20 ml 10% hydrochloric acid, and the pH is adjusted to 9 with 2N sodium hydroxide. The layers are separated, the aqueous layer is washed with 4×50 ml dichloromethane, and the combined organics are dried over potassium carbonate. The dried organics are concentrated in vacuo to give 3.47 g (87%) of 1-(1-hydroxyethyl)-5,6,7,8-tetrahydroisoquinoline.

1. dry with materialdried 100 ml two neck round bottom flask under nitrogen
2. temperatureto reflux for 1 h
3. temperatureThe mixture is cooled
4. customis quenched with 20 ml 10% hydrochloric acid
5. customThe layers are separated
6. washthe aqueous layer is washed with 4×50 ml dichloromethane
7. dry with materialthe combined organics are dried over potassium carbonate
8. concentrationThe dried organics are concentrated in vacuo

ORD record

ord-de97c4a2141c46f89aa60dde30f9f809

Source dataset

uspto-grants-2000_03

DOI

10.6084/m9.figshare.5104873.v1

Patent number

US06043248