Methanol--water (1/1) → Ethyl 3-methyl-7-(4,5,6,7-tetrahydro-4,4,7,7-tetramethylbenzo[b]thien-2-yl)-2,4,6-octatrienoate

HRID 485034Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 485034
[Br-].[CH3:2][C:3]1([CH3:35])[C:11]2[CH:10]=[C:9]([CH:12]([P+](C3C=CC=CC=3)(C3C=CC=CC=3)C3C=CC=CC=3)[CH3:13])[S:8][C:7]=2[C:6]([CH3:34])([CH3:33])[CH2:5][CH2:4]1.[CH:36]([CH:38]=[CH:39][C:40]([CH3:47])=[CH:41][C:42]([O:44][CH2:45][CH3:46])=[O:43])=O.CO.O>C1OCCC1>[CH3:47][C:40]([CH:39]=[CH:38][CH:36]=[C:12]([C:9]1[S:8][C:7]2[C:6]([CH3:33])([CH3:34])[CH2:5][CH2:4][C:3]([CH3:2])([CH3:35])[C:11]=2[CH:10]=1)[CH3:13])=[CH:41][C:42]([O:44][CH2:45][CH3:46])=[O:43]

Komponenten

5

Edukt 3

HCID 22242641Methanol--water (1/1)HCID 23049224[1-(4,5,6,7-Tetrahydro-4,4,7,7-tetramethylbenzo-[b]thien-2-yl)ethyl]triphenylphosphonium bromideHCID 54439227Ethyl 5-formyl-3-methyl-2,4-pentadienoate

Produkt 1

HCID 53882835Ethyl 3-methyl-7-(4,5,6,7-tetrahydro-4,4,7,7-tetramethylbenzo[b]thien-2-yl)-2,4,6-octatrienoateAusbeute 83,3 %

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 8028TetrahydrofuranLösungsmittel

Versuchsvorschrift

4.50 g of [1-(4,5,6,7-tetrahydro-4,4,7,7-tetramethylbenzo[b]thien-2-yl)ethyl]triphenylphosphonium bromide and 1.3 g of ethyl 5-formyl-3-methylpenta-2,4-dienoate are dissolved in 70 ml of butylene oxide and the solution is heated at reflux for 2 hours. The cooled mixture is poured into a methanol/water mixture (6:4) and extracted several times with hexane. The hexane phase is washed three times with water, dried and evaporated. After filtration of the crude product over silica gel (eluting agent hexane/ether 9:1), there are obtained 2.4 g of ethyl 3-methyl-7-(4,5,6,7-tetrahydro-4,4,7,7-tetramethylbenzo[b]thien-2-yl)-2,4,6-octatrienoate as a pale yellowish oil.

Aufarbeitung

  1. temperaturethe solution is heated
  2. temperatureat reflux for 2 hours
  3. extractionextracted several times with hexane
  4. washThe hexane phase is washed three times with water
  5. customdried
  6. customevaporated
  7. filtrationAfter filtration of the crude product over silica gel (eluting agent hexane/ether 9:1), there

Quellen und Nachweise

ORD-Eintrag
ord-2f8184d7ebc54610ad76464104b2859b
Quelldatensatz
uspto-grants-1985_08
Patentnummer
US04535086

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