Water → HCID 60144043, compound

HRID 337348Notes

Reaction equation

HRID 337348 reaction equation
[CH3:1][C:2]1[CH:6]=[C:5]([CH3:7])[N:4]([C:8]2[CH:13]=[CH:12][C:11]([C:14](OC)=[O:15])=[CH:10][C:9]=2[OH:18])[N:3]=1.[BH4-].[Li+].O>O1CCCC1>[CH3:1][C:2]1[CH:6]=[C:5]([CH3:7])[N:4]([C:8]2[CH:13]=[CH:12][C:11]([CH2:14][OH:15])=[CH:10][C:9]=2[OH:18])[N:3]=1

Participants

5

Reactant 3

HCID 962WaterHCID 4148881Lithium borohydrideHCID 86703252HCID 86703252, compound

Product 1

HCID 60144043HCID 60144043, compoundYield 10.6%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Conditions

Temperature
50 °C

Procedure

132 mg of methyl 4-(3,5-dimethyl-1H-pyrazol-yl)-3-hydroxybenzene carboxylate was dissolved in 2.6 ml of tetrahydrofuran, and 58 mg of lithium borohydride was added and stirred at 50° C. for 3.5 hours. To the reaction mixture was added 20 ml of water, and extracted with 20 ml of ethyl acetate. After the organic layer was dried over anhydrous magnesium sulfate, the solvent was distilled off under reduced pressure, and purified using preparative thin-layer silica gel column chromatography (hexane:ethyl acetate=1:2) to yield 12.4 mg of the title compound.

Workup

  1. extractionextracted with 20 ml of ethyl acetate
  2. dry with materialAfter the organic layer was dried over anhydrous magnesium sulfate
  3. distillationthe solvent was distilled off under reduced pressure
  4. custompurified

Sources & evidence

ORD record
ord-8677210d56e14677ac412d7c8f0233d2
Source dataset
uspto-grants-2014_11
Patent number
US08889727B2

Reaction notes

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