Potassium trimethylsilanolate → HCID 66788306, compound
Reaction equation
[Br:1][C:2]1[CH:3]=[C:4]([C:8]2([C:11]([O:13]C)=[O:12])[CH2:10][CH2:9]2)[CH:5]=[N:6][CH:7]=1.C[Si](C)(C)[O-].[K+:20]>C1COCC1>[Br:1][C:2]1[CH:3]=[C:4]([C:8]2([C:11]([O-:13])=[O:12])[CH2:9][CH2:10]2)[CH:5]=[N:6][CH:7]=1.[K+:20]Participants
4
Reactant 2
Product 1
Reagents, catalysts & solvents 1
Procedure
To a solution of methyl 1-(5-bromopyridin-3-yl)cyclopropanecarboxylate (4.764 g, 18.6 mmol) in THF (190 mL) was added 90% potassium trimethylsilanolate (2.65 g, 18.6 mmol) and the reaction mixture was stirred at room temperature over night. Then, the mixture was filtered and washed with THF to give the desired product (2.668 g) as a light brown solid. The mother liquors were concentrated to around 50 mL of THF. Another portion of 90% potassium trimethylsilanolate (0.43 g) was added and stirring was continued for 5 h at room temperature. Then, the mixture was filtered and washed again with THF to give a second batch of desired product (0.953 g) which was combined with the first batch to give the title compound (3.621 g, 59.1%) as a light brown solid. MS:242.0 and 244.1 (M+H+).