Sodium Hydroxide → 1-(4-Ethynylbenzyl)pyrrolidine

Reaction equation

C[Si]([C:5]#[C:6][C:7]1[CH:18]=[CH:17][C:10]([CH2:11][N:12]2[CH2:16][CH2:15][CH2:14][CH2:13]2)=[CH:9][CH:8]=1)(C)C.[OH-].[Na+]>ClCCl.CO>[C:6]([C:7]1[CH:18]=[CH:17][C:10]([CH2:11][N:12]2[CH2:16][CH2:15][CH2:14][CH2:13]2)=[CH:9][CH:8]=1)#[CH:5]

Participants

Procedure

A solution of 0.75 g (2.91 mmol) of 1-(4-trimethylsilanylethynylbenzyl)pyrrolidine in 10 mL of dichloromethane and 10 mL of methanol is combined with 2.4 mL of a 1M sodium hydroxide solution and stirred for 3 hours at ambient temperature. The reaction mixture is evaporated down and the residue is extracted with water and ethyl acetate. The organic phase is stirred with activated charcoal, filtered, and then dried over sodium sulfate. Yield: 0.4 g (74.1% of theory); C13H15N (M=185.27); calc.: molecular ion peak (M+H)+: 186; found: molecular ion peak (M+H)+: 186.