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Triethyl phosphonoacetate → HCID 21473739, Verbindung

HRID 742308
Notizen
Druckvorschau

Reaktionsgleichung

Reaktionsgleichung von HRID 742308
[H-].[Na+].C(OP([CH2:11][C:12]([O:14][CH2:15][CH3:16])=[O:13])(OCC)=O)C.[CH:17]([C:19]1[S:23][C:22]([C:24]([O:26][C:27]([CH3:30])([CH3:29])[CH3:28])=[O:25])=[CH:21][CH:20]=1)=O>CCCCCC.O1CCCC1.C(OCC)C>[CH2:15]([O:14][C:12](/[CH:11]=[CH:17]/[C:19]1[S:23][C:22]([C:24]([O:26][C:27]([CH3:30])([CH3:29])[CH3:28])=[O:25])=[CH:21][CH:20]=1)=[O:13])[CH3:16]
KomponentenVersuchsvorschriftAufarbeitungQuellen und NachweiseNotizen zur Reaktion

Komponenten

7

Edukt 3

HCID 13345Triethyl phosphonoacetateHCID 24758Sodium hydrideHCID 21473735Tert-butyl 5-formylthiophene-2-carboxylate

Produkt 1

HCID 21473739HCID 21473739, Verbindung

Reagenzien, Katalysatoren, Lösungsmittel 3

HCID 3283Diethyl EtherLösungsmittelHCID 8028
Tetrahydrofuran
Lösungsmittel
3×
HCID 8058HexaneLösungsmittel

Versuchsvorschrift

Sodium hydride (min 60% paraffinic dispersion, 1.88 g, about 47 mmol) was washed with anhydrous hexane in a nitrogen stream and suspended in anhydrous tetrahydrofuran. The obtained suspension was stirred under cooling with ice, followed by the gradual dropwise addition of a solution of ethyl diethylphosphonoacetate (10.53 g, 47 mmol) in anhydrous tetrahydrofuran. The obtained mixture was stirred at room temperature for 15 minutes. A solution of the t-butyl 5-formyl-2-thiophenecarboxylate (6.65 g, 31.3 mmol) prepared above in anhydrous tetrahydrofuran was gradually dropped into the resulting mixture under cooling with ice. The obtained mixture was stirred at room temperature for 30 minutes, diluted with diethyl ether, washed with a dilute alkali, diluted hydrochloric acid and an aqueous solution of common salt, dehydrated and evaporated in a vacuum to dryness. The residue was purified by silica gel column chromatography (developer: n-hexane/ethyl acetate=8:1) to give the objective compound. yield: 7.58 g

Aufarbeitung

  1. temperatureunder cooling with ice
  2. stirringThe obtained mixture was stirred at room temperature for 15 minutes
  3. additionwas gradually dropped into the resulting mixture
  4. temperatureunder cooling with ice
  5. stirringThe obtained mixture was stirred at room temperature for 30 minutes
  6. washwashed with a dilute alkali, diluted hydrochloric acid
  7. customevaporated in a vacuum to dryness
  8. customThe residue was purified by silica gel column chromatography (developer: n-hexane/ethyl acetate=8:1)
  9. customto give the objective compound

Quellen und Nachweise

ORD-Eintrag
ord-8569fc7ae7484a12bb1f9a0615ac6a73
Quelldatensatz
uspto-grants-1996_09
DOI
10.6084/m9.figshare.5104873.v1
Patentnummer
US05554615

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