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Water → ethyl 3-[1-(4-benzyloxybenzyl)-3-(4-benzyloxybenzyloxy)-1H-pyrazol-4-yl]propionate

HRID 350206
Notizen
Druckvorschau

Reaktionsgleichung

Reaktionsgleichung von HRID 350206
C(OP([CH2:9][C:10]([O:12][CH2:13][CH3:14])=[O:11])(OCC)=O)C.[H-].[Na+].[CH2:17]([O:24][C:25]1[CH:54]=[CH:53][C:28]([CH2:29][N:30]2[CH:34]=[C:33]([CH:35]=O)[C:32]([O:37][CH2:38][C:39]3[CH:44]=[CH:43][C:42]([O:45][CH2:46][C:47]4[CH:52]=[CH:51][CH:50]=[CH:49][CH:48]=4)=[CH:41][CH:40]=3)=[N:31]2)=[CH:27][CH:26]=1)[C:18]1[CH:23]=[CH:22][CH:21]=[CH:20][CH:19]=1.O>O1CCCC1>[CH2:17]([O:24][C:25]1[CH:54]=[CH:53][C:28]([CH2:29][N:30]2[CH:34]=[C:33]([CH2:35][CH2:9][C:10]([O:12][CH2:13][CH3:14])=[O:11])[C:32]([O:37][CH2:38][C:39]3[CH:44]=[CH:43][C:42]([O:45][CH2:46][C:47]4[CH:52]=[CH:51][CH:50]=[CH:49][CH:48]=4)=[CH:41][CH:40]=3)=[N:31]2)=[CH:27][CH:26]=1)[C:18]1[CH:19]=[CH:20][CH:21]=[CH:22][CH:23]=1
KomponentenVersuchsvorschriftAufarbeitungQuellen und NachweiseNotizen zur Reaktion

Komponenten

6

Edukt 4

HCID 962WaterHCID 13345Triethyl phosphonoacetateHCID 24758Sodium hydrideHCID 230247931-(4-benzyloxybenzyl)-3-(4-benzyloxybenzyloxy)-1H-pyrazole-4-carbaldehyde

Produkt 1

HCID 23024835ethyl 3-[1-(4-benzyloxybenzyl)-3-(4-benzyloxybenzyloxy)-1H-pyrazol-4-yl]propionateAusbeute 95 %

Reagenzien, Katalysatoren, Lösungsmittel

1
HCID 8028TetrahydrofuranLösungsmittel2×

Versuchsvorschrift

To a solution of ethyl diethylphosphonoacetate (2.74 ml) in tetrahydrofuran (50 ml), sodium hydride (60%, oily, 552 mg) was added at 0° C., and then the solution was stirred at room temperature for 30 minutes. To the reaction mixture, a solution of 1-(4-benzyloxybenzyl)-3-(4-benzyloxybenzyloxy)-1H-pyrazol-4-carbaldehyde (6.31 g) in tetrahydrofuran (100 ml) was added slowly, and the solution was stirred at room temperature for 15 minutes. The reaction mixture was poured into water, which was extracted with ethyl acetate. The ethyl acetate layer was washed with dilute hydrochloric acid, then, with saturated aqueous sodium chloride solution, and dried (MgSO4) and concentrated. The obtained crystals were collected by filtration, and ethyl 3-[1-(4-benzyloxybenzyl)-3-(4-benzyloxybenzyloxy)-1H-pyrazol-4-yl]propionate (6.79 g, yield: 95%) was obtained. This was recrystallized from ethyl acetate-hexane. Melting point: 98–99° C.

Aufarbeitung

  1. stirringthe solution was stirred at room temperature for 15 minutes
  2. extractionwas extracted with ethyl acetate
  3. washThe ethyl acetate layer was washed with dilute hydrochloric acid
  4. dry with materialwith saturated aqueous sodium chloride solution, and dried (MgSO4)
  5. concentrationconcentrated
  6. filtrationThe obtained crystals were collected by filtration

Quellen und Nachweise

ORD-Eintrag
ord-44db36ce8e6246d0b96c2691479b628b
Quelldatensatz
uspto-grants-2007_02
DOI
10.6084/m9.figshare.5104873.v1
Patentnummer
US07179823B1

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