Sodium Hydroxide → 3-[4-(1-Pyrrolidinyl)phenyl]-1-(5,6,7,8-tetrahydronaphthalen-2-yl)-2-propen-1-one

Participants

Reaction Steps

A solution of 2.6 g of 1 (15 mmol), 2.6 g of p-pyrrolidinylbenzaldehyde (15 mmol), and 0.66 g of sodium hydroxide in 100 ml of ethanol was stirred under nitrogen at 50° for 24 hr. The reaction mixture was cooled in an ice bath, and the precipitated yellow solid 3-[4-(1-pyrrolidinyl)phenyl]-1-(5,6,7,8-tetrahydronaphthalen-2-yl)-2-propen-1-one was collected by filtration and washed with cold ethanol. Yield: 3.2 g (64%); m.p. 167° to 169°. λmax (CHCl3): 420 nm (ε=36,800); 330 nm (4,300); 276 nm (16,400). Calcd for C23H25NO: C, 83.34; H, 7.60; N, 4.23. Found: C, 82.68, 82.67; H, 7.57, 7.55; N, 4.03, 4.15.

Provenance & Evidence