p-(2-(Dimethylamino)ethoxy)benzaldehyde → 2-[p-[(E)-2-(3,4-dihydro-4,4-dimethyl-2H--benzothiopyran-6-yl)propenyl]phenoxy]-N,N-dimethylethylamine

HRID 37441

Reaktionsgleichung

Reaktionsgleichung von HRID 37441
[Br-].[CH3:2][C:3]1([CH3:34])[C:12]2[C:7](=[CH:8][CH:9]=[C:10]([CH:13]([P+](C3C=CC=CC=3)(C3C=CC=CC=3)C3C=CC=CC=3)[CH3:14])[CH:11]=2)[S:6][CH2:5][CH2:4]1.C([Li])CCC.[CH3:40][N:41]([CH3:53])[CH2:42][CH2:43][O:44][C:45]1[CH:52]=[CH:51][C:48]([CH:49]=O)=[CH:47][CH:46]=1>O1CCCC1>[CH3:34][C:3]1([CH3:2])[C:12]2[CH:11]=[C:10](/[C:13](/[CH3:14])=[CH:49]/[C:48]3[CH:51]=[CH:52][C:45]([O:44][CH2:43][CH2:42][N:41]([CH3:40])[CH3:53])=[CH:46][CH:47]=3)[CH:9]=[CH:8][C:7]=2[S:6][CH2:5][CH2:4]1

Komponenten

5

Edukt 3

HCID 84823p-(2-(Dimethylamino)ethoxy)benzaldehydeHCID 19935432[1-(4,4-Dimethyl-6-thiochromanyl)ethyl]triphenylphosphonium bromideHCID 178418339Butyllithium

Produkt 1

HCID 677834662-[p-[(E)-2-(3,4-dihydro-4,4-dimethyl-2H--benzothiopyran-6-yl)propenyl]phenoxy]-N,N-dimethylethylamineAusbeute 44,1 %

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 8028TetrahydrofuranLösungsmittel2×

Reaktionsbedingungen

Temperatur
0 °C

Versuchsvorschrift

32 g of [1-(4,4-dimethyl-6-thiochromanyl)ethyl]triphenylphosphonium bromide were suspended in 130 ml of tetrahydrofuran and treated at 0° C. with 37 ml of n-butyllithium (1.6 molar in hexane). After stirring at 0° C. for 45 minutes, a solution of 10 g of 4-(2-dimethylaminoethoxy)benzaldehyde in 60 ml of tetrahydrofuran was added dropwise to the orange reaction mixture. The mixture was stirred at room temperature for an additional 1 hour, poured on to ice/water and extracted with ether. The organic phases were washed with water, dried and evaporated. After filtration of the crude product over neutral Alox (eluting agent ether) and recrystallization from hexane/ether, there were obtained 8.7 g of 2-[p-[(E)-2-(3,4-dihydro-4,4-dimethyl-2H-1-benzothiopyran-6-yl)propenyl]phenoxy]-N,N-dimethylethylamine, melting point 81°-82° C.

Aufarbeitung

  1. stirringThe mixture was stirred at room temperature for an additional 1 hour
  2. extractionextracted with ether
  3. washThe organic phases were washed with water
  4. customdried
  5. customevaporated
  6. filtrationAfter filtration of the crude product
  7. washover neutral Alox (eluting agent ether) and recrystallization from hexane/ether

Quellen und Nachweise

ORD-Eintrag
ord-60610fa263774d419fa3d8889eeb31c1
Quelldatensatz
uspto-grants-1995_05
Patentnummer
US05420273

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