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Triethylamine → 2-methoxy-4-[(E)-2-methoxycarbonyl-vinyl]-phenyl 4-[6-(2-methyl-acryloyloxy)-hexyloxy]-benzoate

HRID 1872307
Notizen
Druckvorschau

Reaktionsgleichung

Reaktionsgleichung von HRID 1872307
[CH3:1][C:2](=[CH2:22])[C:3]([O:5][CH2:6][CH2:7][CH2:8][CH2:9][CH2:10][CH2:11][O:12][C:13]1[CH:21]=[CH:20][C:16]([C:17]([O-:19])=[O:18])=[CH:15][CH:14]=1)=[O:4].S(Cl)(Cl)=O.O[C:28]1[CH:39]=[CH:38][C:31]([CH:32]=[CH:33][C:34]([O:36][CH3:37])=[O:35])=[CH:30][C:29]=1[O:40][CH3:41].C(N(CC)CC)C>CN(C=O)C.C1COCC1>[CH3:22][C:2](=[CH2:1])[C:3]([O:5][CH2:6][CH2:7][CH2:8][CH2:9][CH2:10][CH2:11][O:12][C:13]1[CH:14]=[CH:15][C:16]([C:17]([O:19][C:28]2[CH:39]=[CH:38][C:31](/[CH:32]=[CH:33]/[C:34]([O:36][CH3:37])=[O:35])=[CH:30][C:29]=2[O:40][CH3:41])=[O:18])=[CH:20][CH:21]=1)=[O:4]
KomponentenReaktionsbedingungenVersuchsvorschriftAufarbeitungQuellen und NachweiseNotizen zur Reaktion

Komponenten

7

Edukt 4

HCID 8471TriethylamineHCID 16830Methyl 4-hydroxy-3-methoxy-cinnamateHCID 24386Thionyl ChlorideHCID 70216454-[6-(2-Methyl-acryloyloxy)-hexyloxy]-benzoate

Produkt 1

HCID 183291832-methoxy-4-[(E)-2-methoxycarbonyl-vinyl]-phenyl 4-[6-(2-methyl-acryloyloxy)-hexyloxy]-benzoateAusbeute 50,8 %

Reagenzien, Katalysatoren, Lösungsmittel

2
HCID 6228DimethylformamideKatalysatorHCID 8028TetrahydrofuranLösungsmittel

Reaktionsbedingungen

Temperatur
90 °C

Versuchsvorschrift

8.5 g (0.028 mol) of 4-[6-(2-methyl-acryloyloxy)-hexyloxy]-benzoate were treated with 6 ml of thionyl chloride and 3 drops of DMF and the mixture was heated to 90° C. for 2 hours. The excess thionyl chloride was completely removed firstly in a water-jet vacuum and subsequently in a high vacuum. The residual acid chloride was taken up in 20 ml of dichloromethane and slowly added dropwise at 0° C. to a solution of 5.25 g (0.025 mol) of methyl 4-hydroxy-3-methoxy-cinnamate and 4.25 ml of triethylamine in 25 ml of THF. The batch was stirred at room temperature overnight, filtered and the filtrate was evaporated to dryness. The residue was purified by column chromatography on silica gel with dichloromethane/diethyl ether (19:1) and subsequently by recrystallization from ethanol/THF. 6.31 g of 2-methoxy-4-[(E)-2-methoxycarbonyl-vinyl]-phenyl 4-[6-(2-methyl-acryloyloxy)-hexyloxy]-benzoate were isolated as a white powder; m.p. 92-94° C.

Aufarbeitung

  1. customThe excess thionyl chloride was completely removed firstly in a water-jet vacuum and subsequently in a high vacuum
  2. filtrationfiltered
  3. customthe filtrate was evaporated to dryness
  4. customThe residue was purified by column chromatography on silica gel with dichloromethane/diethyl ether (19:1) and subsequently by recrystallization from ethanol/THF

Quellen und Nachweise

ORD-Eintrag
ord-62f38aa2bfe545c8b5dd6142fcea5a7e
Quelldatensatz
uspto-grants-2000_08
DOI
10.6084/m9.figshare.5104873.v1
Patentnummer
US06107427

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