HCID 22313290, Verbindung → HCID 22313309, Verbindung

HRID 965839Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 965839
[CH2:1]([O:4][C:5]1[CH:6]=[C:7]([CH:12]=[CH:13][C:14]=1[CH:15]=[CH2:16])[C:8]([O:10][CH3:11])=[O:9])C=C>C(Cl)Cl.C1CCC(P(C2CCCCC2)C2CCCCC2)CC1.C1CCC(P(C2CCCCC2)C2CCCCC2)CC1.C1C=CC(C=[Ru](Cl)Cl)=CC=1>[O:4]1[C:5]2[C:14](=[CH:13][CH:12]=[C:7]([C:8]([O:10][CH3:11])=[O:9])[CH:6]=2)[CH:15]=[CH:16][CH2:1]1

Komponenten

4

Edukt 1

HCID 22313290HCID 22313290, Verbindung

Produkt 1

HCID 22313309HCID 22313309, VerbindungAusbeute 64 %

Reagenzien, Katalysatoren, Lösungsmittel 2

HCID 11967259Benzylidenebis(tricyclohexylphosphine)dichlororutheniumKatalysatorHCID 6344DichloromethaneLösungsmittel

Versuchsvorschrift

To a stirred solution of methyl 3-(allyloxy)-4-vinylbenzoate (0.67 g, 3.1 mmol) in CH2Cl2 (20 mL) at rt is added benzylidene-bis(tricyclohexylphosphine)dichlororuthenium (63 mg, 0.076 mmol). The mixture is stirred at rt for 2 h. The reaction mixture is concentrated in vacuo to a dark residue. The crude product is purified by flash chromatography on SiO2. Elution with hexanes-EtOAc (95:5) gives 372 mg (64%) of methyl 2H-chromene-7-carboxylate as a clear oil: 1H NMR (400 MHz, CDCl3) δ 7.56, 7.46, 7.01, 6.46, 5.91, 4.89, 3.91.

Aufarbeitung

  1. concentrationThe reaction mixture is concentrated in vacuo to a dark residue
  2. customThe crude product is purified by flash chromatography on SiO2
  3. washElution with hexanes-EtOAc (95:5)

Quellen und Nachweise

ORD-Eintrag
ord-e5ea8b4738e942db84c52dd5edad3d2f
Quelldatensatz
uspto-grants-2005_10
Patentnummer
US06951868B2

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