Methyl Acrylate → Methyl 5-Acetoxy-2-formyl-4-methoxycinnamate

HRID 1898760Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 1898760
[C:1]([O:4][C:5]1[CH:12]=[C:11](Br)[C:8]([CH:9]=[O:10])=[CH:7][C:6]=1[O:14][CH3:15])(=[O:3])[CH3:2].C(N(CC)CC)C.[C:23]([O:27][CH3:28])(=[O:26])[CH:24]=[CH2:25]>CN(C=O)C.CCOCC.O.C1(C=CC=CC=1)[P](C1C=CC=CC=1)(C1C=CC=CC=1)[Pd][P](C1C=CC=CC=1)(C1C=CC=CC=1)C1C=CC=CC=1>[C:1]([O:4][C:5]1[C:6]([O:14][CH3:15])=[CH:7][C:8]([CH:9]=[O:10])=[C:11]([CH:12]=1)[CH:25]=[CH:24][C:23]([O:27][CH3:28])=[O:26])(=[O:3])[CH3:2]

Komponenten

8

Edukt 3

HCID 7294Methyl AcrylateHCID 8471TriethylamineHCID 2623485-Bromo-4-formyl-2-methoxyphenyl acetate

Produkt 1

HCID 53756943Methyl 5-Acetoxy-2-formyl-4-methoxycinnamate

Reagenzien, Katalysatoren, Lösungsmittel 4

HCID 178419050HCID 178419050, VerbindungKatalysatorHCID 962WaterLösungsmittelHCID 3283Diethyl EtherLösungsmittelHCID 6228DimethylformamideLösungsmittel

Reaktionsbedingungen

Temperatur
135 °C

Versuchsvorschrift

To a degassed solution of 4-acetoxy-6-bromo-3-methoxybenzaldehyde (15.4 g), and bis(triphenylphosphine)palladium (11) (1.2 g) in DMF (150 ml) is added triethylamine (31.9 ml) and methyl acrylate (19.6 g). The mixture is heated 135° C. for about 1.5 hours, cooled to room temperature and diluted with ether and water. The organic layer is washed with water, brine, dried over magnesium sulfate, filtered and concentrated in vacuo. The residue is purified by HPLC, eluting with 33% ethyl acetate in hexanes, then methylene chloride, to give the desired product.

Aufarbeitung

  1. temperaturecooled to room temperature
  2. washThe organic layer is washed with water, brine
  3. dry with materialdried over magnesium sulfate
  4. filtrationfiltered
  5. concentrationconcentrated in vacuo
  6. customThe residue is purified by HPLC
  7. washeluting with 33% ethyl acetate in hexanes

Quellen und Nachweise

ORD-Eintrag
ord-6d60ba4013af443b98f7ff64911150e8
Quelldatensatz
uspto-grants-1996_11
Patentnummer
US05571506

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