Triethylamine → 3-(1-tert-butyl-5-(4-chlorophenyl)-1H-pyrazol-3-yl)propan-1-ol

HRID 387177Notes

Reaction equation

HRID 387177 reaction equation
[Cl:1][C:2]1[CH:7]=[CH:6][C:5]([C:8](=O)[CH2:9][C:10](=O)[CH2:11][CH2:12][CH2:13][OH:14])=[CH:4][CH:3]=1.[C:17]([NH:21][NH2:22])([CH3:20])([CH3:19])[CH3:18].Cl.C(N(CC)CC)C>CO>[C:17]([N:21]1[C:8]([C:5]2[CH:6]=[CH:7][C:2]([Cl:1])=[CH:3][CH:4]=2)=[CH:9][C:10]([CH2:11][CH2:12][CH2:13][OH:14])=[N:22]1)([CH3:20])([CH3:19])[CH3:18]

Participants

5

Reactant 3

HCID 8471TriethylamineHCID 81889tert-Butylhydrazine monohydrochlorideHCID 144974141-(4-Chlorophenyl)-6-hydroxyhexan-1,3-dione2×

Product 1

HCID 685612533-(1-tert-butyl-5-(4-chlorophenyl)-1H-pyrazol-3-yl)propan-1-ol

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent2×

Conditions

Temperature
40 °C

Procedure

1-(4-chlorophenyl)-6-hydroxyhexane-1,3-dione (2.0 g, 8.310 mmol) was dissolved in 15 mL of methanol. t-BuNHNH2.HCl (2.1 g, 16.620 mmol) was dissolved in 15 mL of methanol and then added with triethylamine (TEA; 2.3 mL, 16.620 mmol). After they were all dissolved, the mixture was added into a solution of 1-(4-chlorophenyl)-6-hydroxyhexane-1,3-dione, and then stirred for 14 hours at 40° C. The reaction progress and completion were confirmed by TLC. Upon completion of the reaction, while the temperature was kept at room temperature, the solvent was removed under reduced pressure. The reaction residue was diluted with EtOAc, and added with water. The aqueous layer was extracted with EtOAc and the organic layer was dried with anhydrous MgSO4 and filtered and concentrated under reduced pressure. The concentrate was separated by column chromatography (EtOAc:Hexane=2:3, v/v) to obtain 1.57 g (64%) of target compound.

Workup

  1. customUpon completion of the reaction
  2. customwas kept at room temperature
  3. customthe solvent was removed under reduced pressure
  4. additionThe reaction residue was diluted with EtOAc
  5. additionadded with water
  6. extractionThe aqueous layer was extracted with EtOAc
  7. dry with materialthe organic layer was dried with anhydrous MgSO4
  8. filtrationfiltered
  9. concentrationconcentrated under reduced pressure
  10. customThe concentrate was separated by column chromatography (EtOAc
  11. customHexane=2:3, v/v) to obtain 1.57 g (64%) of target compound

Sources & evidence

ORD record
ord-861baa8558a54cba8478cc7819a4dcf1
Source dataset
uspto-grants-2013_02
Patent number
US08372844B2

Reaction notes

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