Borane → HCID 86692421, compound

HRID 1748450Notes

Reaction equation

HRID 1748450 reaction equation
B.[CH2:2]([O:4][C:5]([C:7]1[CH:8]=[N:9][N:10]([C:13]2[CH:21]=[CH:20][C:16]([C:17](O)=[O:18])=[CH:15][CH:14]=2)[C:11]=1[CH3:12])=[O:6])[CH3:3].C(=O)(O)[O-].[Na+]>O1CCCC1>[CH2:2]([O:4][C:5]([C:7]1[CH:8]=[N:9][N:10]([C:13]2[CH:14]=[CH:15][C:16]([CH2:17][OH:18])=[CH:20][CH:21]=2)[C:11]=1[CH3:12])=[O:6])[CH3:3]

Participants

5

Reactant 3

HCID 6331BoraneHCID 516892Sodium BicarbonateHCID 16770921877675-70-2

Product 1

HCID 86692421HCID 86692421, compoundYield 67.8%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent2×

Procedure

0.93M Tetrahydrofuran solution of borane (18 ml) was added dropwise to a solution of 4-[4-(ethoxycarbonyl)-5-methyl-1H-pyrazol-1-yl]benzoic acid (3.0 g) in tetrahydrofuran (50 ml) at 0° C. and stirred at room temperature for three hours. After completion of the reaction, a saturated aqueous solution of sodium bicarbonate was added therein and extracted with ethyl acetate three times. The organic layer was washed with saturated brine, dried oner anhydrous sodium sulfate and concentrated in vacuo. The resulting residue was purified with NH silica gel column chromatography (n-hexene/ethyl acetate) to give 1-[4-(hydroxymethyl)phenyl]-5-methyl-1H-pyrazole-4-carboxylic acid ethyl ester (1.93 g) as a white solid.

Workup

  1. customAfter completion of the reaction
  2. extractionextracted with ethyl acetate three times
  3. washThe organic layer was washed with saturated brine
  4. dry with materialdried oner anhydrous sodium sulfate
  5. concentrationconcentrated in vacuo
  6. customThe resulting residue was purified with NH silica gel column chromatography (n-hexene/ethyl acetate)

Sources & evidence

ORD record
ord-14cbcffbbe6d43e69affdeb36d9678a9
Source dataset
uspto-grants-2015_10
Patent number
US09150555B2

Reaction notes

Loading…