Potassium trimethylsilanolate → HCID 66788306, compound

HRID 1774812Notes

Reaction equation

HRID 1774812 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

HCID 23668039Potassium trimethylsilanolateHCID 59578399Methyl 1-(5-bromopyridin-3-yl)cyclopropanecarboxylate

Product 1

HCID 66788306HCID 66788306, compoundYield 51.2%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

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+).

Workup

  1. filtrationThen, the mixture was filtered
  2. washwashed with THF

Sources & evidence

ORD record
ord-0e8346542914448392cca0180901333a
Source dataset
uspto-grants-2016_02
Patent number
US09260408B2

Reaction notes

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