Water → Triadimenol-tert-butylhydroxy
Reaction equation
[Cl:1][C:2]1[CH:21]=[CH:20][C:5]([O:6][CH:7]([N:15]2[CH:19]=[N:18][CH:17]=[N:16]2)[C:8](=[O:14])[C:9]([CH3:13])([CH3:12])[CH2:10][OH:11])=[CH:4][CH:3]=1.[BH4-].[Na+].O.C(Cl)Cl>C(O)(C)C>[Cl:1][C:2]1[CH:3]=[CH:4][C:5]([O:6][CH:7]([N:15]2[CH:19]=[N:18][CH:17]=[N:16]2)[CH:8]([OH:14])[C:9]([CH3:12])([CH3:13])[CH2:10][OH:11])=[CH:20][CH:21]=1Participants
Procedure
25 g (0.08 mol) of 1-(4-chlorophenoxy)-1-(1,2,4-triazol-1-yl)-3,3-dimethyl-4-hydroxy-butan-2-one were dissolved in 350 ml of isopropanol, and 3.5 g of sodium borohydride were added in portions at room temperature. The mixture was stirred at room temperature for 15 hours, 500 ml of water were added, the mixture was stirred at room temperature for a further 15 hours, 300 ml of methylene chloride were added and the organic phase was washed three times with 100 ml of water each time. The organic phase was dried over sodium sulphate, the solvent was distilled off under a waterpump vacuum and 100 ml of ether were added to the residue. 17 g (67.6% of theory) of 1-(4-chlorophenoxy)-1-(1,2,4-triazol-1-yl)-3,3-dimethyl-butane-2,4-diol were obtained as colorless crystals of melting point 110°-112° C. ##STR19##
Workup
- stirringthe mixture was stirred at room temperature for a further 15 hours
- washthe organic phase was washed three times with 100 ml of water each time
- dry with materialThe organic phase was dried over sodium sulphate
- distillationthe solvent was distilled off under a waterpump vacuum and 100 ml of ether
- additionwere added to the residue
Sources & evidence
- ORD record
- ord-a3246066df934bcdb734d5e1ca7c885a
- Source dataset
- uspto-grants-1981_03
- Patent number
- US04254132
Reaction notes
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