Triethylamine → 3-(4-Hydroxymethylphenyl)acrylic acid ethyl ester

HRID 2218117Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 2218117
Br[C:2]1[CH:9]=[CH:8][C:5]([CH2:6][OH:7])=[CH:4][CH:3]=1.C1(P(C2C=CC=CC=2)C2C=CC=CC=2)C=CC=CC=1.C(N(CC)CC)C.[C:36]([O:40][CH2:41][CH3:42])(=[O:39])[CH:37]=[CH2:38]>C([O-])(=O)C.[Pd+2].C([O-])(=O)C>[CH2:41]([O:40][C:36](=[O:39])[CH:37]=[CH:38][C:2]1[CH:9]=[CH:8][C:5]([CH2:6][OH:7])=[CH:4][CH:3]=1)[CH3:42]

Komponenten

6

Edukt 4

HCID 8471TriethylamineHCID 8821Ethyl AcrylateHCID 11776TriphenylphosphineHCID 701194-Bromobenzyl alcohol

Produkt 1

HCID 684575823-(4-Hydroxymethylphenyl)acrylic acid ethyl ester

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 167845palladium(II) acetateKatalysator

Versuchsvorschrift

4-Bromobenzyl alcohol (10.5 g, 56.1 mmol), triphenylphosphine (0.5 g, 1.9 mmol) and palladium acetate (0.5 g, 2.2 mmol) were stirred at reflux in ethyl acrylate (20 mL) and triethylamine (100 mL) for 72 hours, then allowed to cool. The reaction mixture was filtered through celite (Diatomaceous Earth), then concentrated. The crude solid was purified by chromatography on silica gel (20% v/v ethyl acetate in petroleum ether) to afford the title compound as an oil.

Aufarbeitung

  1. temperatureto cool
  2. filtrationThe reaction mixture was filtered through celite (Diatomaceous Earth)
  3. concentrationconcentrated
  4. customThe crude solid was purified by chromatography on silica gel (20% v/v ethyl acetate in petroleum ether)

Quellen und Nachweise

ORD-Eintrag
ord-cec32b817e254fb298ae4f7643043384
Quelldatensatz
uspto-grants-2008_08
Patentnummer
US07410984B2

Notizen zur Reaktion

Wird geladen…