Methanol → 2-(4-Phenyl-3-p-tolyl-1H-pyrazol-5-yl)ethanol

HRID 1471933Notes

Reaction equation

HRID 1471933 reaction equation
[CH2:1]([C:4]1[NH:8][N:7]=[C:6]([C:9]2[CH:14]=[CH:13][C:12]([CH3:15])=[CH:11][CH:10]=2)[C:5]=1[C:16]1[CH:21]=[CH:20][CH:19]=[CH:18][CH:17]=1)[CH:2]=C.ClCCl.[BH4-].[Na+].C[OH:28]>>[C:16]1([C:5]2[C:6]([C:9]3[CH:14]=[CH:13][C:12]([CH3:15])=[CH:11][CH:10]=3)=[N:7][NH:8][C:4]=2[CH2:1][CH2:2][OH:28])[CH:21]=[CH:20][CH:19]=[CH:18][CH:17]=1

Participants

5

Reactant 4

HCID 887MethanolHCID 6344DichloromethaneHCID 4311764Sodium borohydrideHCID 673845665-Allyl-4-phenyl-3-p-tolyl-1H-pyrazole

Product 1

HCID 673850292-(4-Phenyl-3-p-tolyl-1H-pyrazol-5-yl)ethanol

Procedure

5-Allyl-4-phenyl-3-p-tolyl-1H-pyrazole (1.0 g, 3.64 mmol) was dissolved in methanol (40 mL) and dichloromethane (10 mL) and cooled to −78° C. on a dry-ice/acetone bath. Ozone was bubbled through the solution for h, until the solution appeared light blue. To the reaction was added sodium borohydride (0.138 g, 3.64 mmol) and the reaction was removed from the dry-ice bath and stirred at room temperature for 1 h. Excess solvent was removed under reduced pressure and the reaction was extracted with EtOAc/H2O, dried over MgSO4, and purified by column chromatography to give the title compound as white solid (0.54 g). LCMS m/z=279.2 [M+H]+; 1H NMR (400 MHz, DMSO-d6) δ ppm 2.25 (s, 3H), 2.71 (t, J=7.33 Hz, 2H), 3.57 (t, J=7.33 Hz, 2H), 4.65 (bs, 1H), 7.03-7.09 (m, 2H), 7.16-7.23 (m, 3H), 7.24-7.31 (m, 2H), 7.32-7.40 (m, 2H).

Workup

  1. customOzone was bubbled through the solution for h, until the solution
  2. customthe reaction was removed from the dry-ice bath
  3. customExcess solvent was removed under reduced pressure
  4. extractionthe reaction was extracted with EtOAc/H2O
  5. dry with materialdried over MgSO4
  6. custompurified by column chromatography

Sources & evidence

ORD record
ord-68c95bb6ada64975a2bbe4bdf90fee40
Source dataset
uspto-grants-2015_04
Patent number
US09012478B2

Reaction notes

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