Triethylamine → 8-(1-(4-Chlorophenyl)-5-(p-tolyl)-1H-pyrazol-3-yl)-1,4-dioxaspiro[4.5]decan-8-ol

HRID 1802526Notes

Reaction equation

HRID 1802526 reaction equation
Cl.[Cl:2][C:3]1[CH:8]=[CH:7][C:6]([NH:9][NH2:10])=[CH:5][CH:4]=1.C(N(CC)CC)C.[OH:18][C:19]1([C:29]#[C:30][C:31]([C:33]2[CH:38]=[CH:37][C:36]([CH3:39])=[CH:35][CH:34]=2)=O)[CH2:28][CH2:27][C:22]2([O:26][CH2:25][CH2:24][O:23]2)[CH2:21][CH2:20]1>C(O)C>[Cl:2][C:3]1[CH:8]=[CH:7][C:6]([N:9]2[C:31]([C:33]3[CH:34]=[CH:35][C:36]([CH3:39])=[CH:37][CH:38]=3)=[CH:30][C:29]([C:19]3([OH:18])[CH2:28][CH2:27][C:22]4([O:23][CH2:24][CH2:25][O:26]4)[CH2:21][CH2:20]3)=[N:10]2)=[CH:5][CH:4]=1

Participants

5

Reactant 3

HCID 8471TriethylamineHCID 71600Hydrazine, (4-chlorophenyl)-, hydrochloride (1:1)HCID 583993813-(8-Hydroxy-1,4-dioxaspiro[4.5]decan-8-yl)-1-(p-tolyl)-2-propyn-1-one

Product 1

HCID 583994018-(1-(4-Chlorophenyl)-5-(p-tolyl)-1H-pyrazol-3-yl)-1,4-dioxaspiro[4.5]decan-8-olYield 96.1%

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent2×

Procedure

To a solution of 4-chlorophenylhydrazine hydrochloride (418 mg, 2.33 mmol) in ethanol (4.8 mL), triethylamine (5.87 mL, 42.1 mmol) was added dropwise, and the obtained solution was stirred at room temperature for 30 minutes. To the reaction solution, a solution of 3-(8-hydroxy-1,4-dioxaspiro[4.5]decan-8-yl)-1-(p-tolyl)-2-propyn-1-one (Reference Example 15) (698 mg, 2.32 mmol) in ethanol (4.7 mL) was added dropwise, and the obtained solution was stirred at room temperature for 14 hours. Thereafter, the reaction solution was concentrated under reduced pressure. Water was added to the residue and the resultant was extracted with ethyl acetate. The organic layer was washed with distilled water and brine, dried over anhydrous sodium sulfate and concentrated under reduced pressure. The residue was purified by flash chromatography (silica gel, n-hexane/ethyl acetate) to obtain the captioned compound (948 mg, 2.23 mmol, yield: 96%) as an amorphous product.

Workup

  1. stirringthe obtained solution was stirred at room temperature for 14 hours
  2. concentrationThereafter, the reaction solution was concentrated under reduced pressure
  3. additionWater was added to the residue
  4. extractionthe resultant was extracted with ethyl acetate
  5. washThe organic layer was washed with distilled water and brine
  6. dry with materialdried over anhydrous sodium sulfate
  7. concentrationconcentrated under reduced pressure
  8. customThe residue was purified by flash chromatography (silica gel, n-hexane/ethyl acetate)

Sources & evidence

ORD record
ord-817366c53d1245c681a0ecd85dde8875
Source dataset
uspto-grants-2013_01
Patent number
US08349874B2

Reaction notes

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