Sodium hydride → 5-(t-Butoxycarbonylmethyl)oxy-2-hydroxymethylpyridine
Reaction equation
[OH:1][C:2]1[CH:3]=[CH:4][C:5]([CH2:8][OH:9])=[N:6][CH:7]=1.[H-].[Na+].Br[CH2:13][C:14]([O:16][C:17]([CH3:20])([CH3:19])[CH3:18])=[O:15]>CN(C=O)C.C(OCC)(=O)C>[C:17]([O:16][C:14]([CH2:13][O:1][C:2]1[CH:3]=[CH:4][C:5]([CH2:8][OH:9])=[N:6][CH:7]=1)=[O:15])([CH3:20])([CH3:19])[CH3:18]Participants
Procedure
The solution of 5-hydroxy-2-hydroxymethylpyridine (5.0 g) in DMF (10 ml) was titrated under ice-cooling in the suspension of sodium hydride (60% purity, 1.6 g) in DMF (10 ml). After 10 minutes, the mixture was heated to room temperature and stirred for 15 minutes. After t-butyl bromoacetate (6 ml) was added to the mixture under ice-cooling, the resulting mixture was stirred under ice-cooling for 10 minutes and at room temperature for 45 minutes. The reaction mixture was diluted with ethyl acetate, washed with water and brine and dried over anhydrous magnesium sulfate. After the solvents were removed by distillation, the residue was purified by column chromatography on silica gel with an eluent system of chloroform→chloroform: methanol=50:1 to give 8.16 g of 5-(t-butoxycarbonylmethyl)oxy-2-hydroxymethylpyridine (yield, 85%).
Workup
- temperaturecooling
- stirringthe resulting mixture was stirred under ice-
- temperaturecooling for 10 minutes and at room temperature for 45 minutes
- washwashed with water and brine
- dry with materialdried over anhydrous magnesium sulfate
- customAfter the solvents were removed by distillation
- customthe residue was purified by column chromatography on silica gel with an eluent system of chloroform→chloroform
Sources & evidence
- ORD record
- ord-4ae1f98634054382bc41edef27873657
- Source dataset
- uspto-grants-1997_01
- Patent number
- US05594004
Reaction notes
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