Diethyl Ether → 3-(1-Hydroxyethyl)-5,6,7,8-tetrahydroisoquinoline

5,6,7,8,-Tetrahydroisoquinoline-3-carbaldehyde (1.2 g, 7.44 mmole) is dissolved in 15 ml tetrahydrofuran at 0° C. in an oven dried 100 ml two neck round bottom flask under nitrogen. The solution is treated with methylmagnesium bromide in diethyl ether (3.7 ml, 11.2 mmole) followed by 10 ml diethyl ether. The reaction mixture is warmed to room temperature and then to reflux for 1 h. The mixture was 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 4×25 ml dichloromethane, and the combined organics are dried over potassium carbonate. The dried organics are concentrated in vacuo to give 1.30 g (99%) of the 3-(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 was cooled
4. customis quenched with 20 ml 10% hydrochloric acid
5. customThe layers are separated
6. washthe aqueous layer is washed with 4×25 ml dichloromethane
7. dry with materialthe combined organics are dried over potassium carbonate
8. concentrationThe dried organics are concentrated in vacuo

ORD record

ord-cc40715958994efebac7c9eaeb7b47e6

Source dataset

uspto-grants-2000_03

DOI

10.6084/m9.figshare.5104873.v1

Patent number

US06043248