Acetic Acid → 1-(4-Chlorophenyl)-4,4-dimethyl-2-(1,2,4-triazole-1-yl)-pentene-3-ol

HRID 579761ノート

反応式

HRID 579761 の反応式
[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.[BH4-].[Na+].O.C(O)(=O)C>CO>[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]=1

参加物

6

反応物 4

HCID 176Acetic AcidHCID 962WaterHCID 4311764Sodium borohydrideHCID 540228171-(4-Chlorophenyl)-4,4-dimethyl-2-(1,2,4-triazol-1-yl)-1-penten-3-one

生成物 1

HCID 917371-(4-Chlorophenyl)-4,4-dimethyl-2-(1,2,4-triazole-1-yl)-pentene-3-ol収率 69%

試薬・触媒・溶媒 1

HCID 887Methanol溶媒

実験手順

The II-A isomer (2.9 g, 0.01 mole; m.p. 108°-109° C.) of 1-(4-chlorophenyl)-4,4-dimethyl-2-(1,2,4-triazole-1-yl)-1-pentene-3-one (Compound No. 1') was dissolved in methanol (50 ml). Sodium borohydride (0.38 g, 0.01 mole) was added thereto while keeping the temperature of the reaction solution at 20° C. or less with ice-cooling. The reaction mixture was kept at 20° C. for 3 hours, and then decomposed with addition of water (100 ml) and acetic acid (1 ml). The organic layer was extracted with ethyl acetate (100 ml), and the extract was washed with a 5% aqueous sodium hydrogen carbonate solution (50 ml) and dried over anhydrous sodium sulfate. The solvent was then removed under reduced pressure, and the residue obtained was recrystallized from isopropanol to obtain 2.0 g (yield 69%) of the I'-A isomer having a melting point of 153°-155° C. The elementary analysis and NMR spectrum of the compound are shown below.

後処理

  1. customat 20° C. or less
  2. temperaturecooling
  3. extractionThe organic layer was extracted with ethyl acetate (100 ml)
  4. washthe extract was washed with a 5% aqueous sodium hydrogen carbonate solution (50 ml)
  5. dry with materialdried over anhydrous sodium sulfate
  6. customThe solvent was then removed under reduced pressure
  7. customthe residue obtained
  8. customwas recrystallized from isopropanol
  9. customto obtain 2.0 g (yield 69%) of the I'-A isomer

出典と根拠

ORDレコード
ord-ad1bb8b54d5347bdb962993426138355
出典データセット
uspto-grants-1988_06
特許番号
US04749716

反応ノート

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