Sodium borohydride → {4-[4-(2-Ethoxy-naphthalen-1-ylmethyl)-3,5-diethyl-pyrazol-1-yl]-3,5-dimethylphenyl}-methanol

HRID 1740112Notes

Reaction equation

HRID 1740112 reaction equation
[BH4-].[Na+].[CH2:3]([O:5][C:6]1[CH:15]=[CH:14][C:13]2[C:8](=[CH:9][CH:10]=[CH:11][CH:12]=2)[C:7]=1[CH2:16][C:17]1[C:18]([CH2:34][CH3:35])=[N:19][N:20]([C:24]2[C:31]([CH3:32])=[CH:30][C:27]([CH:28]=[O:29])=[CH:26][C:25]=2[CH3:33])[C:21]=1[CH2:22][CH3:23])[CH3:4]>CO>[CH2:3]([O:5][C:6]1[CH:15]=[CH:14][C:13]2[C:8](=[CH:9][CH:10]=[CH:11][CH:12]=2)[C:7]=1[CH2:16][C:17]1[C:18]([CH2:34][CH3:35])=[N:19][N:20]([C:24]2[C:25]([CH3:33])=[CH:26][C:27]([CH2:28][OH:29])=[CH:30][C:31]=2[CH3:32])[C:21]=1[CH2:22][CH3:23])[CH3:4]

Participants

4

Reactant 2

HCID 4311764Sodium borohydrideHCID 218373184-[4-(2-Ethoxy-naphthalen-1-ylmethyl)-3,5-diethyl-pyrazol-1-yl]-3,5-dimethyl-benzaldehyde

Product 1

HCID 21837352{4-[4-(2-Ethoxy-naphthalen-1-ylmethyl)-3,5-diethyl-pyrazol-1-yl]-3,5-dimethylphenyl}-methanolYield 13.2%

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Procedure

Sodium borohydride (0.127 g, 3.35 mmol) was added to a solution of 4-[4-(2-ethoxy-naphthalen-1-ylmethyl)-3,5-diethyl-pyrazol-1-yl]-3,5-dimethyl-benzaldehyde (0.370 g, 8.4 mmol) in 10 ml of methanol. After stirring 30 minutes, the reaction was quenched by addition of 1 ml of brine. The solvent was removed in vacuo, and the residue was extracted with methylene chloride/brine (10 ml of each). The aqueous phase was then twice extracted with 10 ml portions of fresh methylene chloride. The combined organic extracts were dried over anhydrous sodium sulfate and concentrated in vacuo to afford an oil (490 mg). Flash chromatography of the entire sample (silica gel, 40 micron mesh; elution with ethyl acetate/hexanes=1:1 in volume) yielded the title compound (380 mg) as an oily colorless solid.

Workup

  1. customthe reaction was quenched by addition of 1 ml of brine
  2. customThe solvent was removed in vacuo
  3. extractionthe residue was extracted with methylene chloride/brine (10 ml of each)
  4. extractionThe aqueous phase was then twice extracted with 10 ml portions of fresh methylene chloride
  5. dry with materialThe combined organic extracts were dried over anhydrous sodium sulfate
  6. concentrationconcentrated in vacuo

Sources & evidence

ORD record
ord-422515c97e6e43859dbf9a95ca4e94af
Source dataset
uspto-grants-1999_10
Patent number
US05968944

Reaction notes

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