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Hydrochloric Acid → HCID 15839226, Verbindung

HRID 743987
Notizen
Druckvorschau

Reaktionsgleichung

Reaktionsgleichung von HRID 743987
C(NC(C)C)(C)C.[Li]CCCC.CCCCCC.[CH2:19]1[O:27][C:26]2[CH:25]=[CH:24][C:23]([CH2:28][CH2:29][C:30]([O:32][CH3:33])=[O:31])=[CH:22][C:21]=2[O:20]1.[C:34]([C:42]1[CH:47]=[CH:46][CH:45]=[CH:44][CH:43]=1)(=[O:41])[C:35]1[CH:40]=[CH:39][CH:38]=[CH:37][CH:36]=1.Cl>C1COCC1>[C:42]1([C:34]([C:35]2[CH:36]=[CH:37][CH:38]=[CH:39][CH:40]=2)([OH:41])[CH:29]([CH2:28][C:23]2[CH:24]=[CH:25][C:26]3[O:27][CH2:19][O:20][C:21]=3[CH:22]=2)[C:30]([O:32][CH3:33])=[O:31])[CH:43]=[CH:44][CH:45]=[CH:46][CH:47]=1
KomponentenReaktionsbedingungenVersuchsvorschriftAufarbeitungQuellen und NachweiseNotizen zur Reaktion

Komponenten

8

Edukt 6

HCID 313Hydrochloric AcidHCID 3102BenzophenoneHCID 7912DiisopropylamineHCID 8058HexaneHCID 10081775Methyl 3-(3,4-methylenedioxyphenyl)-propionateHCID 178418339Butyllithium

Produkt 1

HCID 15839226
HCID 15839226, Verbindung
Ausbeute 76 %

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 8028TetrahydrofuranLösungsmittel3×

Reaktionsbedingungen

Temperatur
-78 °C

Versuchsvorschrift

To a solution of di-isopropylamine (0.52 ml, 3.69 mmol) in dry THF (3 ml) at 0° C. under argon was added n-BuLi in hexane (1.36 ml, 2.5 M, 3.4 mmol). After stirring for 40 min the solution was cooled to -78° C. and a solution of methyl 3-(3,4-methylenedioxyphenyl)-propanoate (0.592 g, 2.84 mmol) in dry THF (2 ml) was added dropwise over 7 min. After a further 2 min a solution of benzophenone (0.517 g, 2.84 mmol) in dry THF (2 ml) was added dropwise. After a further 30 min at -78° C. the mixture was warmed to 0° C. over 30 min and poured into 1M aqueous HCl. The product was extracted with EtOAc (3X). The combined organic extract was washed with water (2X) then brine. After drying (Na2SO4 anhydrous), filtration and evaporation gave an off-white solid. Recrystallization from hot hexane gave the title compound (0.835 g, 76% yield) as a colorless solid.

Aufarbeitung

  1. temperatureAfter a further 30 min at -78° C. the mixture was warmed to 0° C. over 30 min
  2. extractionThe product was extracted with EtOAc (3X)
  3. extractionThe combined organic extract
  4. washwas washed with water (2X)
  5. customAfter drying
  6. filtration(Na2SO4 anhydrous), filtration and evaporation
  7. customgave an off-white solid
  8. customRecrystallization from hot hexane

Quellen und Nachweise

ORD-Eintrag
ord-e165b3663b4044d0993691f0cffb21c8
Quelldatensatz
uspto-grants-1996_09
DOI
10.6084/m9.figshare.5104873.v1
Patentnummer
US05559105

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