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

HRID 888280Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 888280
Cl.[CH3:2][O:3][C:4]1[CH:9]=[CH:8][C:7]([NH:10][NH2:11])=[CH:6][CH:5]=1.C(N(CC)CC)C.[OH:19][C:20]1([C:30]#[C:31][C:32]([C:34]2[CH:39]=[CH:38][C:37]([CH3:40])=[CH:36][CH:35]=2)=O)[CH2:29][CH2:28][C:23]2([O:27][CH2:26][CH2:25][O:24]2)[CH2:22][CH2:21]1>C(O)C>[CH3:2][O:3][C:4]1[CH:9]=[CH:8][C:7]([N:10]2[C:32]([C:34]3[CH:35]=[CH:36][C:37]([CH3:40])=[CH:38][CH:39]=3)=[CH:31][C:30]([C:20]3([OH:19])[CH2:29][CH2:28][C:23]4([O:24][CH2:25][CH2:26][O:27]4)[CH2:22][CH2:21]3)=[N:11]2)=[CH:6][CH:5]=1

Komponenten

5

Edukt 3

HCID 8471TriethylamineHCID 27239044-Methoxyphenylhydrazine hydrochlorideHCID 583993813-(8-Hydroxy-1,4-dioxaspiro[4.5]decan-8-yl)-1-(p-tolyl)-2-propyn-1-one

Produkt 1

HCID 672961338-(1-(4-Methoxyphenyl)-5-(p-tolyl)-1H-pyrazol-3-yl)-1,4-dioxaspiro[4.5]decan-8-olAusbeute 91,4 %

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 702EthanolLösungsmittel2×

Versuchsvorschrift

To a solution of 4-methoxyphenylhydrazine hydrochloride (7.35 g, 42.1 mmol) in ethanol (76.6 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) (11.5 g, 38.3 mmol) in ethanol (76.6 mL) was added dropwise, and the obtained solution was stirred at room temperature for 15 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 1 M hydrochloric acid, distilled water and brine, dried over anhydrous magnesium sulfate and concentrated under reduced pressure. The residue was purified by flash chromatography (silica gel, n-hexane/ethyl acetate) to obtain the captioned compound (14.7 g, 35.0 mmol, 91%) as an amorphous product.

Aufarbeitung

  1. stirringthe obtained solution was stirred at room temperature for 15 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 1 M hydrochloric acid
  6. distillationdistilled water and brine
  7. dry with materialdried over anhydrous magnesium sulfate
  8. concentrationconcentrated under reduced pressure
  9. customThe residue was purified by flash chromatography (silica gel, n-hexane/ethyl acetate)

Quellen und Nachweise

ORD-Eintrag
ord-f2aa626af44c4443a21621ea466e123f
Quelldatensatz
uspto-grants-2012_08
Patentnummer
US08247569B2

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