Methanol → 3-(4-Phenyl-3-p-tolyl-1H-pyrazol-5-yl)propan-1-ol

HRID 1471893ノート

反応式

HRID 1471893 の反応式
[CH2:1]([C:5]1[NH:9][N:8]=[C:7]([C:10]2[CH:15]=[CH:14][C:13]([CH3:16])=[CH:12][CH:11]=2)[C:6]=1[C:17]1[CH:22]=[CH:21][CH:20]=[CH:19][CH:18]=1)[CH2:2][CH:3]=C.[BH4-].[Na+].C[OH:26]>C(Cl)Cl>[C:17]1([C:6]2[C:7]([C:10]3[CH:15]=[CH:14][C:13]([CH3:16])=[CH:12][CH:11]=3)=[N:8][NH:9][C:5]=2[CH2:1][CH2:2][CH2:3][OH:26])[CH:22]=[CH:21][CH:20]=[CH:19][CH:18]=1

参加物

5

反応物 3

HCID 887MethanolHCID 4311764Sodium borohydrideHCID 673853415-(But-3-enyl)-4-phenyl-3-p-tolyl-1H-pyrazole

生成物 1

HCID 673849033-(4-Phenyl-3-p-tolyl-1H-pyrazol-5-yl)propan-1-ol

試薬・触媒・溶媒 1

HCID 6344Dichloromethane溶媒

反応条件

温度
-78 °C

実験手順

5-(But-3-enyl)-4-phenyl-3-p-tolyl-1H-pyrazole (360 mg, 1.248 mmol) was dissolved in MeOH (20 mL) and DCM (5 mL). The reaction was cooled to −78° C. and ozone was bubbled through the solution. After the starting material was consumed, the reaction was cooled in an ice bath. Sodium borohydride (70.8 mg, 1.872 mmol) was added to the reaction. The reaction was warmed to room temperature and stirred for an hour. The solvent was removed under reduced pressure and the reaction was extracted (50 mL each of H2O and EtOAc). The aqueous layer was extracted again with EtOAc (50 mL). The combined organic layer was dried, concentrated, and the residue was purified by silica gel column chromatography to give the title compound (130 mg) as a white solid. LCMS m/z=293.1 [M+H]+; 1H NMR (400 MHz, DMSO-d6) δ ppm 1.60-1.74 (m, 2H), 2.25 (s, 3H), 2.54-2.62 (m, 2H), 3.33-3.44 (m, 2H), 4.44 (br. s., 1H), 7.16 (t, J=6.44 Hz, 6H), 7.24-7.30 (m, 1H), 7.32-7.38 (m, 2H), 12.71 (s, 1H).

後処理

  1. customozone was bubbled through the solution
  2. customAfter the starting material was consumed
  3. temperaturethe reaction was cooled in an ice bath
  4. temperatureThe reaction was warmed to room temperature
  5. customThe solvent was removed under reduced pressure
  6. extractionthe reaction was extracted (50 mL each of H2O and EtOAc)
  7. extractionThe aqueous layer was extracted again with EtOAc (50 mL)
  8. customThe combined organic layer was dried
  9. concentrationconcentrated
  10. customthe residue was purified by silica gel column chromatography

出典と根拠

ORDレコード
ord-8b157c8a272241fa8e7adfc3657d0cb2
出典データセット
uspto-grants-2015_04
特許番号
US09012478B2

反応ノート

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