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Ethyl Acetate → 5-Cyano-6-(2-nitro-5-phenoxy-phenyl)-4-(tetrahydro-pyran-4-yl)-hex-5-enoic acid

HRID 252441
Notizen
Druckvorschau

Reaktionsgleichung

Reaktionsgleichung von HRID 252441
[C:1]([CH:3](P(OCC)(OCC)=O)[CH:4]([CH:10]1[CH2:15][CH2:14][O:13][CH2:12][CH2:11]1)[CH2:5][CH2:6][C:7]([OH:9])=[O:8])#[N:2].[H-].[Na+].[N+:26]([C:29]1[CH:36]=[CH:35][C:34]([O:37][C:38]2[CH:43]=[CH:42][CH:41]=[CH:40][CH:39]=2)=[CH:33][C:30]=1[CH:31]=O)([O-:28])=[O:27].C(OCC)(=O)C>C1COCC1>[C:1]([C:3](=[CH:31][C:30]1[CH:33]=[C:34]([O:37][C:38]2[CH:43]=[CH:42][CH:41]=[CH:40][CH:39]=2)[CH:35]=[CH:36][C:29]=1[N+:26]([O-:28])=[O:27])[CH:4]([CH:10]1[CH2:11][CH2:12][O:13][CH2:14][CH2:15]1)[CH2:5][CH2:6][C:7]([OH:9])=[O:8])#[N:2]
KomponentenVersuchsvorschriftAufarbeitungQuellen und NachweiseNotizen zur Reaktion

Komponenten

6

Edukt 4

HCID 8857Ethyl AcetateHCID 24758Sodium hydrideHCID 442030822-Nitro-5-phenoxybenzaldehydeHCID 594281685-Cyano-5-(diethoxy-phosphoryl)-4-(tetrahydro-pyran-4-yl)-pentanoic acid

Produkt 1

HCID 672694525-Cyano-6-(2-nitro-5-phenoxy-phenyl)-4-(tetrahydro-pyran-4-yl)-hex-5-enoic acid

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 8028TetrahydrofuranLösungsmittel

Versuchsvorschrift

To a solution of 5-cyano-5-(diethoxy-phosphoryl)-4-(tetrahydro-pyran-4-yl)-pentanoic acid (2.68 g, 7.7 mmol) in THF (300 mL), sodium hydride (60%, 1.24 g) was added portionwise at room temperature. 2-Nitro-5-phenoxy-benzaldehyde (1.9 g, 7.7 mmol) was then added, and the reaction mixture was stirred at room temperature overnight. Ethyl acetate was added to the reaction mixture, and the resulting solution was washed with saturated aqueous NH4Cl solution. The organic phase was separated, dried with MgSO4, and filtered. The filtrate was evaporated in vacuo to yield an oil which was triturated with heptane to yield the title compound as a solid.

Aufarbeitung

  1. washthe resulting solution was washed with saturated aqueous NH4Cl solution
  2. customThe organic phase was separated
  3. dry with materialdried with MgSO4
  4. filtrationfiltered
  5. customThe filtrate was evaporated in vacuo
  6. customto yield an oil which
  7. customwas triturated with heptane

Quellen und Nachweise

ORD-Eintrag
ord-c6dbd89354154073b916246c7e6fd9b6
Quelldatensatz
uspto-grants-2011_01
DOI
10.6084/m9.figshare.5104873.v1
Patentnummer
US07868022B2

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