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

HRID 1471893Notes

Reaction equation

HRID 1471893 reaction equation
[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

Participants

5

Reactant 3

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

Product 1

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

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Conditions

Temperature
-78 °C

Procedure

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).

Workup

  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

Sources & evidence

ORD record
ord-8b157c8a272241fa8e7adfc3657d0cb2
Source dataset
uspto-grants-2015_04
Patent number
US09012478B2

Reaction notes

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