Tetrahydrofuran → HCID 58409914, compound
Reaction equation
[N:1]1([C:6]2[CH:18]=[C:17]([C:19]3[CH:24]=[CH:23][C:22]([CH3:25])=[CH:21][CH:20]=3)[C:16]3[C:15]4[C:10](=[CH:11][CH:12]=[CH:13][CH:14]=4)[CH2:9][C:8]=3[C:7]=2[C:26]#[N:27])[CH2:5][CH2:4][CH2:3][CH2:2]1.[H-].[Na+].C1C[O:33]CC1>>[O:33]=[C:9]1[C:8]2[C:7]([C:26]#[N:27])=[C:6]([N:1]3[CH2:5][CH2:4][CH2:3][CH2:2]3)[CH:18]=[C:17]([C:19]3[CH:20]=[CH:21][C:22]([CH3:25])=[CH:23][CH:24]=3)[C:16]=2[C:15]2[C:10]1=[CH:11][CH:12]=[CH:13][CH:14]=2Participants
4
Conditions
- Temperature
- 2.5 °C
Procedure
A solution of 2-(pyrrolidin-1-yl)-4-p-tolyl-9H-fluorene-1-carbonitrile (350 mg) in THF was added sodium hydride (42 mg) and was stirred at 0-5° C. for less than five minutes. After completion, the reaction solvent was evaporated under vacuum and the crude solid obtained was quenched with ice water and subsequently neutralized by dilute HCl. The precipitate thus obtained was filtered and purified on a silica gel column using ethyl acetate-hexane as eluent. Red solid; yield 76%; mp 162-164° C.; ESMS 365 (M++1); IR (KBr) 1716 cm−1 (CO) 2214 (CN).