Sodium Hydroxide → 4-Methyl-5-(oxiran-2-yl)pyridine-3-carbonitrile
Reaction equation
[CH:1]([C:3]1[C:4]([CH3:11])=[C:5]([C:9]#[N:10])[CH:6]=[N:7][CH:8]=1)=[CH2:2].C1C(=O)N(Br)C(=[O:15])C1.[OH-].[Na+]>O>[CH3:11][C:4]1[C:3]([CH:1]2[CH2:2][O:15]2)=[CH:8][N:7]=[CH:6][C:5]=1[C:9]#[N:10]Participants
5
Reactant 3
Product 1
Reagents, catalysts & solvents 1
Conditions
- Temperature
- 40 °C
Procedure
A suspension of 5-ethenyl-4-methylpyridine-3-carbonitrile (3.00 g, 20.8 mmol) in 30 mL of ButOH and 60 mL of water was added NBS (4.6 g, 26 mmol) portionwise. The mixture was stirred at 40° C. for 2.5 hour then cooled down to 10° C. NaOH solution (2.5 g in 70 mL of water, 62.4 mmol) was added dropwise and stirred for 15 minutes. The reaction mixture was extracted with EtOAc twice and condensed. The residue was purified by column chromatography (petrol ether: EtOAc=20:1) to afford 4-methyl-5-(oxiran-2-yl)pyridine-3-carbonitrile.
Workup
- temperaturethen cooled down to 10° C
- stirringstirred for 15 minutes
- extractionThe reaction mixture was extracted with EtOAc twice
- customcondensed
- customThe residue was purified by column chromatography (petrol ether: EtOAc=20:1)
Sources & evidence
- ORD record
- ord-ceb8f59d00734baeb1abebaa80eae0fe
- Source dataset
- uspto-grants-2015_12
- Patent number
- US09206199B2
Reaction notes
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