反应详情

温度

-20 °C

A solution of 5,5,8,8-tetramethyl-5,6,7,8-tetrahydro-naphthalen-2-ylamine (1) (1.0 g, 4.93 mmole) in 12 mL tetrahydrofuran (THF) was cooled to −78° C. and treated dropwise with 2.5 M n-butyllithium solution (2.2 mL) and allowed to warm to −20° C. over a one hour period. Iodopentane (1.28 mL) was introduced at −20° C., the mixture stirred at room temperature for three hours, poured into 50 mL of a saturated aqueous sodium bicarbonate solution and extracted with three portions of 50 mL of ether. The combined organic extracts were dried over MgSO4, filtered and concentrated in vacuo to give a brown oil. The product was purified by flash chromatography (SiO2, 5% ethyl acetate/hexanes) providing 1.1 g (82%) of pentyl-(5,5,8,8-tetramethyl-5,6,7,8-tetrahydro-naphthalen-2-yl)-amine (51) as a colorless oil.

1. extractionextracted with three portions of 50 mL of ether
2. dry with materialThe combined organic extracts were dried over MgSO4
3. filtrationfiltered
4. concentrationconcentrated in vacuo
5. customto give a brown oil
6. customThe product was purified by flash chromatography (SiO2, 5% ethyl acetate/hexanes)