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

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Reaction Steps

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.

Provenance & Evidence