Hydrochloric Acid → 1-(4-Chlorophenyl)-4,4-dimethyl-2-(1,2,4-triazole-1-yl)-pentene-3-ol
Reaction equation
[Cl:1][C:2]1[CH:7]=[CH:6][C:5](/[CH:8]=[C: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:4][CH:3]=1.Cl>ClCCCl>[Cl:1][C:2]1[CH:7]=[CH:6][C:5]([CH:8]=[C:9]([N:16]2[CH:20]=[N:19][CH:18]=[N:17]2)[CH:10]([OH:15])[C:11]([CH3:14])([CH3:13])[CH3:12])=[CH:4][CH:3]=1Participants
Procedure
88 Milligrams (0.53 mmole) of the present compound obtained in Example 1 was dissolved in 2 ml of 1,2-dichloroethane, and 2 ml of a 1,2-dichloroethane solution containing 290 mg (1.0 mmole) of (E)-1-(4-chlorophenyl)-2-(1,2,4-triazol-1-yl)-4,4-dimethyl-1-penten-3-one (E/Z=95.8/4.2) was added dropwise thereto. After reaction at room temperature for 24 hours, 2% hydrochloric acid was added to separate the reaction solution into an aqueous and organic layers. After concentrating the organic layer, the residue was purified by column chromatography on silica gel to obtain 180 mg of 1-(4-chlorophenyl)-2-(1,2,4-triazol-1-yl)-4,4-dimethyl-1-penten-3-ol. The ratio of E-form alcohol to Z-form alcohol was 95.6 to 4.4, and the enantiomer ratio of the E-form alcohol was: (+)-isomer: (-)-isomer=19:81.
Workup
- additionwas added dropwise
- customAfter reaction at room temperature for 24 hours
- customto separate the reaction solution into an aqueous and organic layers
- concentrationAfter concentrating the organic layer
- customthe residue was purified by column chromatography on silica gel
Sources & evidence
- ORD record
- ord-923977247ce744e8bb9360718f69831e
- Source dataset
- uspto-grants-1988_06
- Patent number
- US04749809
Reaction notes
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