Sodium borohydride → HCID 114845940, compound

HRID 1499113Notes

Reaction equation

HRID 1499113 reaction equation
[Cl:1][C:2]1[CH:9]=[CH:8][C:5]([CH:6]=[O:7])=[C:4]([N:10]2[CH:14]=[CH:13][C:12]([CH3:15])=[N:11]2)[CH:3]=1.[BH4-].[Na+]>CO>[Cl:1][C:2]1[CH:9]=[CH:8][C:5]([CH2:6][OH:7])=[C:4]([N:10]2[CH:14]=[CH:13][C:12]([CH3:15])=[N:11]2)[CH:3]=1

Participants

4

Reactant 2

HCID 4311764Sodium borohydrideHCID 114844633HCID 114844633, compound

Product 1

HCID 114845940HCID 114845940, compound

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Conditions

Temperature
0 °C

Procedure

4-Chloro-2-(3-methyl-pyrazol-1-yl)-benzaldehyde (446 mg, 2.03 mmol) from Step 1 was dissolved in MeOH (14 mL) and cooled to 0° C. NaBH4 (175 mg, 4.61 mmol)) was added portionwise. The reaction mixture was allowed to warm to RT, and after 90 min was quenched with acetone. The MeOH was removed in vacuo. The residue was partitioned between water and EtOAc and then extracted. The combined organic layers were washed with brine, dried over Na2SO4, filtered, and concentrated in vacuo. Purification by normal phase silica gel column chromatography (EtOAc/heptane) provided the title compound.

Workup

  1. temperatureto warm to RT
  2. customafter 90 min was quenched with acetone
  3. customThe MeOH was removed in vacuo
  4. customThe residue was partitioned between water and EtOAc
  5. extractionextracted
  6. washThe combined organic layers were washed with brine
  7. dry with materialdried over Na2SO4
  8. filtrationfiltered
  9. concentrationconcentrated in vacuo
  10. customPurification by normal phase silica gel column chromatography (EtOAc/heptane)

Sources & evidence

ORD record
ord-67343303a01d414fbf6247e5bcb36706
Source dataset
uspto-grants-2015_12
Patent number
US09199994B2

Reaction notes

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