Hydrochloric Acid → 1-(6-Chloropyridin-2-yl-oxy)-3,3-dimethyl-1-(1,2,4-triazol-1-yl)butan-2-ol
Reaction equation
[Cl:1][C:2]1[N:7]=[C:6]([O:8][CH:9]([N:16]2[CH:20]=[N:19][CH:18]=[N:17]2)[C:10](=[O:15])[C:11]([CH3:14])([CH3:13])[CH3:12])[CH:5]=[CH:4][CH:3]=1.[BH4-].[Na+].Cl.C(=O)(O)[O-].[Na+]>CO.O>[Cl:1][C:2]1[N:7]=[C:6]([O:8][CH:9]([N:16]2[CH:20]=[N:19][CH:18]=[N:17]2)[CH:10]([OH:15])[C:11]([CH3:12])([CH3:13])[CH3:14])[CH:5]=[CH:4][CH:3]=1Participants
Reactant 4
Product 1
Reagents, catalysts & solvents 2
Procedure
11.8 g (0.04 mol) of 1-(6-chloropyridin-2-yl-oxy)-3,3-dimethyl-1-(1,2,4-triazol-1-yl)-butan-2-one (Example 1) were dissolved in 100 ml of methanol, and 1.8 g (0.04 mol) of sodium borohydride were added in portions at 20°-30° C., while stirring. After the exothermic reaction had ended, 5 ml of concentrated hydrochloric acid were added dropwise and the mixture was stirred at room temperature for 1 hour. Thereafter, 200 ml of water were added and the mixture was neutralised with sodium bicarbonate solution. The reaction mixture was extracted by shaking with ether and the organic phase was dried over sodium sulphate and concentrated. 5.3 g (54% of theory) of 1-(6-chloropyridin-2-yl-oxy)-3,3-dimethyl-1-(1,2,4-triazol-1-yl)butan-2-ol were obtained as a viscous oil in the form of a diastereomer mixture.
Workup
- customAfter the exothermic reaction
- stirringthe mixture was stirred at room temperature for 1 hour
- extractionThe reaction mixture was extracted
- stirringby shaking with ether
- dry with materialthe organic phase was dried over sodium sulphate
- concentrationconcentrated
Sources & evidence
- ORD record
- ord-cd2264a1f89842cc8752d0eead09685a
- Source dataset
- uspto-grants-1983_08
- Patent number
- US04396624
Reaction notes
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