Methanol → HCID 2805406, compound

HRID 1471890Notes

Reaction equation

HRID 1471890 reaction equation
[CH2:1]([C:5]1[NH:9][N:8]=[C:7]([C:10]2[CH:15]=[CH:14][CH:13]=[CH:12][CH:11]=2)[CH:6]=1)[CH2:2][CH:3]=C.[BH4-].[Na+].C[OH:19]>C(Cl)Cl>[C:10]1([C:7]2[CH:6]=[C:5]([CH2:1][CH2:2][CH2:3][OH:19])[NH:9][N:8]=2)[CH:15]=[CH:14][CH:13]=[CH:12][CH:11]=1

Participants

5

Reactant 3

HCID 887MethanolHCID 4311764Sodium borohydrideHCID 11615362HCID 11615362, compound

Product 1

HCID 2805406HCID 2805406, compound

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

5-(But-3-enyl)-3-phenyl-1H-pyrazole (5.4 g, 27.2 mmol) was dissolved in MeOH (40 mL) and DCM (10 mL). The reaction was cooled on a dry-ice/acetone bath and ozone was bubbled through the solution for 2 h. The reaction was transferred into an ice bath and NaBH4 (1.546 g, 40.9 mmol) was added slowly portion-wise (bubbling was observed). Upon complete addition, the reaction was removed from the ice bath and stirred at room temperature for 1 h. Excess solvent was evaporated and the reaction was extracted (100 mL each of H2O and EtOAc). The aqueous layer was extracted again with EtOAc (100 mL). The combined organic layer was dried, concentrated, and the residue was purified by column chromatography to yield the title compound (3.0 g) as a white solid. LCMS m/z=203.3 [M+H]+; 1H NMR (400 MHz, DMSO-d6) δ ppm 1.72-1.82 (m, 2H), 2.54-2.69 (m, 2H), 3.46 (q, J=6.11 Hz, 2H), 4.40-4.54 (m, 1H), 6.45 (s, 1H), 7.21-7.45 (m, 3H), 7.66-7.79 (m, J=7.45 Hz, 2H), 12.53 (s, 1H).

Workup

  1. temperatureThe reaction was cooled on a dry-ice/acetone bath
  2. customozone was bubbled through the solution for 2 h
  3. customThe reaction was transferred into an ice bath
  4. customportion-wise (bubbling was observed)
  5. additionUpon complete addition
  6. customthe reaction was removed from the ice bath
  7. customExcess solvent was evaporated
  8. extractionthe reaction was extracted (100 mL each of H2O and EtOAc)
  9. extractionThe aqueous layer was extracted again with EtOAc (100 mL)
  10. customThe combined organic layer was dried
  11. concentrationconcentrated
  12. customthe residue was purified by column chromatography

Sources & evidence

ORD record
ord-d013bc0ecfb44a75bbe70d9685d00838
Source dataset
uspto-grants-2015_04
Patent number
US09012478B2

Reaction notes

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