Diniconazole synthesis
- Product Name:Diniconazole
- CAS Number:83657-24-3
- Molecular formula:C15H17Cl2N3O
- Molecular Weight:326.22
76713-90-1
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Yield:83657-24-3 98%
Reaction Conditions:
with hydrogenchloride;LiAlH4 in hexane
Steps:
7 Synthesis of (-)-(E)-1-(2,4-dichlorophenyl)-2-(1,2,4-triazol-1-yl)-4,4-dimethyl-1-penten-3-ol:
EXAMPLE 7 Synthesis of (-)-(E)-1-(2,4-dichlorophenyl)-2-(1,2,4-triazol-1-yl)-4,4-dimethyl-1-penten-3-ol: Preparative method (1) (Reaction temperature: -15° C.). Into 10 cc of an ethyl ether solution containing 0.18 g (4.7 mmole) of LiAlH4, was added dropwise 10 cc of an ethyl ether solution containing 0.84 g (4.7 mmole) of (+)-N-methylephedrine over a period of 30 minutes at room temperature, and the mixture was stirred for 20 minutes. To the mixture, while being cooled in ice, was added dropwise 10 cc of an ethyl ether solution containing 1 g (9.4 mmole) of N-methylaniline over a period of 30 minutes, and the mixture was stirred for one hour at room temperature. To the raction mixture cooled at -15° C., was added over a period of 10 minutes 10 cc of an ether solution containing 1 g (3.1 mmole) of (E)-1-(2,4-dichlorophenyl)-2-(1,2,4-triazol-1-yl)-4,4-dimethyl-1-penten-3-one, and the mixture was stirred for 2 hours at -15° C. The mixture was then poured into 100 cc of 1 N hydrochloric acid, extracted with 100 cc of ether, washed successively with an aqueous sodium hydrogencarbonate solution and ice water, dried over anhydrous magnesium sulfate, and stripped of the solvent under reduced pressure. The crystalline residue was collected by filtration using 10 cc of n-hexane and washed to obtain 0.98 g (98% yield) of the captioned compound: [α]D25 -28.0 (c=1, chloroform).
References:
Sumitomo Chemical Company, Limited US4435203, 1984, A
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83657-24-3
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