Triethylamine → 2-(4-Chloro-3,5-dimethoxyphenyl)-4-hydroxymethylpyridine
Reaction equation
[Cl:1][C:2]1[C:7]([O:8][CH3:9])=[CH:6][C:5]([C:10]2[CH:11]=[C:12]([CH:16]=[CH:17][N:18]=2)[C:13](O)=[O:14])=[CH:4][C:3]=1[O:19][CH3:20].C(N(CC)CC)C.ClC(OCC)=O>C1COCC1>[Cl:1][C:2]1[C:3]([O:19][CH3:20])=[CH:4][C:5]([C:10]2[CH:11]=[C:12]([CH2:13][OH:14])[CH:16]=[CH:17][N:18]=2)=[CH:6][C:7]=1[O:8][CH3:9]Participants
5
Procedure
To an ice-cooled solution of 2-(4-chloro-3,5-dimethoxyphenyl)isonicotinic acid (7.20 g) and triethylamine (5.6 mL) in THF (70 mL) was added ethyl chloroformate (2.8 mL). The mixture was stirred at room temperature for 1 hour and filtered. To the filtrate was then added a solution of sodium borohydride (1.25 g) in water (4 mL). The mixture was stirred at room temperature for another hour and evaporated. Water was added to the residue and extracted with chloroform. The organic layer was washed with brine, dried over anhydrous sodium sulfate and evaporated. The residue was subjected to silica gel column chromatography using chloroform-methanol (20:1) and then chloroform-methanol (15:1) to give the title compound.
Workup
- filtrationfiltered
- additionTo the filtrate was then added a solution of sodium borohydride (1.25 g) in water (4 mL)
- stirringThe mixture was stirred at room temperature for another hour
- customevaporated
- additionWater was added to the residue
- extractionextracted with chloroform
- washThe organic layer was washed with brine
- dry with materialdried over anhydrous sodium sulfate
- customevaporated
Sources & evidence
- ORD record
- ord-b78643f1b0c6411da5f16cee794c5037
- Source dataset
- uspto-grants-2005_03
- Patent number
- US06867221B2
Reaction notes
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