4-(2-Morpholinoethoxy)benzaldehyde → 4-[2-[p-[(E)-2-(2,2-dimethyl-1,3-benzodithiol-5-yl)propenyl]phenoxy]ethyl]morpholine

HRID 1463411

Reaktionsgleichung

Reaktionsgleichung von HRID 1463411
[Br-].[CH3:2][C:3]1([CH3:33])[S:7][C:6]2[CH:8]=[CH:9][C:10]([CH:12]([P+](C3C=CC=CC=3)(C3C=CC=CC=3)C3C=CC=CC=3)[CH3:13])=[CH:11][C:5]=2[S:4]1.C([Li])CCC.[O:39]1[CH2:44][CH2:43][N:42]([CH2:45][CH2:46][O:47][C:48]2[CH:55]=[CH:54][C:51]([CH:52]=O)=[CH:50][CH:49]=2)[CH2:41][CH2:40]1>O1CCCC1.CCCCCC>[CH3:33][C:3]1([CH3:2])[S:7][C:6]2[CH:8]=[CH:9][C:10](/[C:12](/[CH3:13])=[CH:52]/[C:51]3[CH:50]=[CH:49][C:48]([O:47][CH2:46][CH2:45][N:42]4[CH2:41][CH2:40][O:39][CH2:44][CH2:43]4)=[CH:55][CH:54]=3)=[CH:11][C:5]=2[S:4]1

Komponenten

6

Edukt 3

HCID 37199024-(2-Morpholinoethoxy)benzaldehydeHCID 19935456[1-(2,2-Dimethyl-1,3-benzodithiol-5-yl)ethyl]triphenylphosphonium bromideHCID 178418339Butyllithium

Produkt 1

HCID 867449624-[2-[p-[(E)-2-(2,2-dimethyl-1,3-benzodithiol-5-yl)propenyl]phenoxy]ethyl]morpholineAusbeute 35,2 %

Reagenzien, Katalysatoren, Lösungsmittel 2

HCID 8028TetrahydrofuranLösungsmittel2×HCID 8058HexaneLösungsmittel

Reaktionsbedingungen

Temperatur
20 °C

Versuchsvorschrift

6.6 g of [1-(2,2-dimethyl-1,3-benzodithiol-5-yl)ethyl]triphenylphosphonium bromide were dissolved in 40 ml of tetrahydrofuran and treated slowly at 0° C. with 9 ml of a 1.5 molar solution of n-butyllithium in hexane. After 40 minutes, 3.5 g of 4-(2-morpholinoethoxy)benzaldehyde in 10 ml of tetrahydrofuran were added dropwise to the dark red solution and the mixture was stirred at 20° C. for 16 hours. The mixture was then poured on to ice and extracted with ethyl acetate. The combined extracts were washed with water, dried and evaporated. After chromatography (silica gel, eluting agent ethyl acetate) and crystallization from ether/hexane, there were obtained 1.8 g of 4-[2-[p-[(E)-2-(2,2-dimethyl-1,3-benzodithiol-5-yl)propenyl]phenoxy]ethyl]morpholine in the form of colorless crystals, melting point 90°-91° C.

Aufarbeitung

  1. additionThe mixture was then poured on to ice
  2. extractionextracted with ethyl acetate
  3. washThe combined extracts were washed with water
  4. customdried
  5. customevaporated
  6. washAfter chromatography (silica gel, eluting agent ethyl acetate) and crystallization from ether/hexane

Quellen und Nachweise

ORD-Eintrag
ord-fbe6296639254d45b685f567006b602e
Quelldatensatz
uspto-grants-1994_04
Patentnummer
US05300522

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