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Ethyl 2-(diethoxyphosphoryl)butanoate → HCID 68850618, Verbindung

HRID 1826073
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Druckvorschau

Reaktionsgleichung

Reaktionsgleichung von HRID 1826073
[CH3:1][CH2:2][CH:3](P(OCC)(OCC)=O)[C:4]([O:6][CH2:7][CH3:8])=[O:5].[CH3:17][C:18](C)([O-])[CH3:19].[K+].[CH3:23][S:24][CH:25]([C:36]1[CH:41]=[C:40](C=O)[CH:39]=[CH:38][C:37]=1[O:44][CH3:45])[C:26]([O:28][CH2:29][C:30]1[CH:35]=[CH:34][CH:33]=[CH:32][CH:31]=1)=[O:27]>O1CCCC1>[CH3:23][S:24][CH:25]([C:36]1[CH:41]=[C:40]([C:3]2([C:4]([O:6][CH2:7][CH3:8])=[O:5])[CH:2]=[CH:1][CH:17]=[CH:18][CH2:19]2)[CH:39]=[CH:38][C:37]=1[O:44][CH3:45])[C:26]([O:28][CH2:29][C:30]1[CH:31]=[CH:32][CH:33]=[CH:34][CH:35]=1)=[O:27]
KomponentenVersuchsvorschriftAufarbeitungQuellen und NachweiseNotizen zur Reaktion

Komponenten

5

Edukt 3

HCID 229053Ethyl 2-(diethoxyphosphoryl)butanoateHCID 11759308HCID 11759308, VerbindungHCID 23665647Potassium tert-butoxide

Produkt 1

HCID 68850618HCID 68850618, VerbindungAusbeute 78 %

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 8028TetrahydrofuranLösungsmittel2×

Versuchsvorschrift

Under an argon atmosphere, triethyl 2-phosphonobutyrate (3.77 g, 14.9 mmol) was dissolved in dehydrated tetrahydrofuran (40 mL) and potassium tert-butoxide (1.68 g, 15.0 mmol) was added under stirring and cooling with ice. After completion of the addition, the mixture was stirred for 1 hour. Following this, benzyl 2-methylthio-2-(5-formyl-2-methoxyphenyl)acetate (4.49 g, 13.6 mmol) dissolved in dehydrated tetrahydrofuran (30 mL) was added and the mixture was stirred for 6 hours at room temperature. The reaction mixture was concentrated and ice water was added, which was made acidic with 1 mol/L hydrochloric acid. The reaction mixture was extracted with ethyl acetate. The extracte was washed with water and brine, dried over anhydrous sodium sulfate, and then concentrated. The residue was purified by silica gel column chromatography (eluent n-hexane:ethyl acetate=9:1 v/v) to afford 4.55 g (78%) of the title compound as a colorless oil.

Aufarbeitung

  1. temperaturecooling with ice
  2. additionAfter completion of the addition
  3. stirringthe mixture was stirred for 1 hour
  4. additionwas added
  5. stirringthe mixture was stirred for 6 hours at room temperature
  6. concentrationThe reaction mixture was concentrated
  7. additionice water was added
  8. extractionThe reaction mixture was extracted with ethyl acetate
  9. washThe extracte was washed with water and brine
  10. dry with materialdried over anhydrous sodium sulfate
  11. concentrationconcentrated
  12. customThe residue was purified by silica gel column chromatography (eluent n-hexane:ethyl acetate=9:1 v/v)

Quellen und Nachweise

ORD-Eintrag
ord-816c8cb23a9745988fe27dd59f50de8f
Quelldatensatz
uspto-grants-2006_05
DOI
10.6084/m9.figshare.5104873.v1
Patentnummer
US07049342B2

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