Potassium Hydroxide → HCID 11208062, compound

Participants

Reaction Steps

A solution of 2,2,2-trifluoro-N-pentyl-N-(5,5,8,8-tetramethyl-5,6,7,8-tetrahydro-naphthalen-2-yl)-acetamide (31) (13.6 g, 37.5 mmole) in 140 mL ethanol was treated with a solution of potassium hydroxide (10.52 g) in 25 mL water. The mixture was stirred at room temperature for two hours, diluted with 100 mL water and then extracted with two 250 mL portions of ethyl acetate. The combined organic extracts were washed with six 200 mL portions of cold water or until the pH was neutral. The organic phase was dried over MgSO4, filtered and concentrated in vacuo to give a yellow oil. The product was purified by flash chromatography (SiO2, 10% ethyl acetate/hexanes) to yield 9.86 g of pentyl-(5,5,8,8-tetramethyl-5,6,7,8-tetrahydro-naphthalen-2-yl)-amine (33) as a golden oil.

Provenance & Evidence