Dimethylformamide → alpha-(2'-(2,3-Epoxypropan-1-yloxy)benzylidene)-gamma-butyrolactone

HRID 2085227Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 2085227
CN(C)C=O.C(=O)([O-])[O-].[K+].[K+].[OH:12][C:13]1[CH:25]=[CH:24][CH:23]=[CH:22][C:14]=1[CH:15]=[C:16]1[CH2:21][CH2:20][O:19][C:17]1=[O:18].S(C1C=CC([N+]([O-])=O)=CC=1)(O[CH2:30][CH:31]1[O:33][CH2:32]1)(=O)=O>O>[O:33]1[CH2:32][CH:31]1[CH2:30][O:12][C:13]1[CH:25]=[CH:24][CH:23]=[CH:22][C:14]=1[CH:15]=[C:16]1[CH2:21][CH2:20][O:19][C:17]1=[O:18]

Komponenten

6

Edukt 4

HCID 6228DimethylformamideHCID 11430Potassium CarbonateHCID 2297583-(2-Hydroxybenzylidene)dihydrofuran-2(3h)-oneHCID 286832Oxiran-2-ylmethyl 4-nitrobenzenesulfonate

Produkt 1

HCID 72642278alpha-(2'-(2,3-Epoxypropan-1-yloxy)benzylidene)-gamma-butyrolactoneAusbeute 99,1 %

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 962WaterLösungsmittel

Reaktionsbedingungen

Temperatur
50 °C

Versuchsvorschrift

Dimethylformamide (30 ml) and potassium carbonate (4.4 g) were added to α-(2′-hydroxybenzylidene)-γ-butyrolactone (3 g), and a racemic compound of glycidyl nosylate (3.4 g) was added. The mixture was stirred at 50° C. for 3 hr. Water was added and the mixture was extracted with ethyl acetate. The organic layer was dried over anhydrous sodium sulfate and concentrated under reduced pressure to give oily α-(2′-(2,3-epoxypropan-1-yloxy)benzylidene)-γ-butyrolactone (3.2 g). This compound (0.4 g) was reacted in methanol with 4-(naphthalen-2-yl)piperidine (0.5 g) in the same manner as in Example 307 to give the title compound, melting point 127-128° C.

Aufarbeitung

  1. extractionthe mixture was extracted with ethyl acetate
  2. dry with materialThe organic layer was dried over anhydrous sodium sulfate
  3. concentrationconcentrated under reduced pressure

Quellen und Nachweise

ORD-Eintrag
ord-9a155643544b4e3fbf66cdc09909e524
Quelldatensatz
uspto-grants-2004_04
Patentnummer
US06720320B2

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