Water → 3-chloro-2H-pyridine-1-carboxylic acid phenyl ester
Reaction equation
[Cl:1][C:2]1[CH:3]=[N:4][CH:5]=[CH:6][CH:7]=1.[BH4-].[Na+].Cl[C:11]([O:13][C:14]1[CH:19]=[CH:18][CH:17]=[CH:16][CH:15]=1)=[O:12].O>CO>[C:14]1([O:13][C:11]([N:4]2[CH:5]=[CH:6][CH:7]=[C:2]([Cl:1])[CH2:3]2)=[O:12])[CH:19]=[CH:18][CH:17]=[CH:16][CH:15]=1Participants
6
Reactant 4
Product 1
Reagents, catalysts & solvents 1
Procedure
To a solution of 3-chloro-pyridine (6.0 g, 53 mmol) in methanol (50 mL) was added NaBH4 (2.6 g, 69 mmol) at −78° C., following addition of phenyl chloroformate (8.3 g, 53 mmol) at same temperature. The mixture was stirred at r.t. for 0.5 h. Then water (200 mL) was added slowly into the solution. The precipitate was collected by filtration to give crude product (Yield: 8.2 g, 67%).
Workup
- filtrationThe precipitate was collected by filtration
Sources & evidence
- ORD record
- ord-16229c5392284f3aacb86bc065ad97e2
- Source dataset
- uspto-grants-2009_02
- Patent number
- US07495007B2
Reaction notes
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