Water → 5-[(4-Methoxyphenyl)methoxy]pyridine-2-carbonitrile
Reaction equation
[H-].[Na+].[CH3:3][O:4][C:5]1[CH:12]=[CH:11][C:8]([CH2:9][OH:10])=[CH:7][CH:6]=1.Br[C:14]1[CH:15]=[CH:16][C:17]([C:20]#[N:21])=[N:18][CH:19]=1.O>CN(C=O)C>[C:20]([C:17]1[CH:16]=[CH:15][C:14]([O:10][CH2:9][C:8]2[CH:11]=[CH:12][C:5]([O:4][CH3:3])=[CH:6][CH:7]=2)=[CH:19][N:18]=1)#[N:21]Participants
Procedure
Sodium hydride (1.44 g, 33 mmol) was dissolved in DMF (20 mL), and 4-methoxybenzyl alcohol (3.74 mL, 33 mmol) was then added to the solution under a nitrogen atmosphere and under ice cooling. The obtained mixture was stirred at room temperature for 30 minutes. Thereafter, 5-bromo-2-cyanopyridine (4.58 g, 25 mmol) was added to the reaction solution, and the obtained mixture was further stirred at room temperature for 30 minutes. Thereafter, water was added to the reaction solution, and it was then extracted with ethyl acetate and washed with water. The water layers were combined and extracted with methylene chloride. The organic layers were combined, were dried over sodium sulfate, and were then concentrated. The obtained residue was recrystallized from ethyl acetate, so as to obtain the title compound (3.57 g, yield: 60%) in the form of yellow crystals.
Workup
- stirringthe obtained mixture was further stirred at room temperature for 30 minutes
- extractionwas then extracted with ethyl acetate
- washwashed with water
- extractionextracted with methylene chloride
- dry with materialwere dried over sodium sulfate
- concentrationwere then concentrated
- customThe obtained residue was recrystallized from ethyl acetate
Sources & evidence
- ORD record
- ord-ac6f4c1b5bcb434cbc140643fc5fec6d
- Source dataset
- uspto-grants-2015_10
- Patent number
- US09150563B2
Reaction notes
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