Tetrahydrofuran → 4-methoxy-3-[3-[3-(methoxyacetylamino)phenyl]-1-oxo-2-propenyl]-2H-1-benzopyran-2-one

HRID 639744

Reaktionsgleichung

Reaktionsgleichung von HRID 639744
O1CCC[CH2:2]1.[OH:6][C:7]1[C:12]2[CH:13]=[CH:14][CH:15]=[CH:16][C:11]=2[O:10][C:9](=[O:17])[C:8]=1[C:18](=[O:33])[CH:19]=[CH:20][C:21]1[CH:26]=[CH:25][CH:24]=[C:23]([NH:27][C:28](=[O:32])[CH2:29][O:30][CH3:31])[CH:22]=1.C1(P(C2C=CC=CC=2)C2C=CC=CC=2)C=CC=CC=1.N(C(OCC)=O)=NC(OCC)=O>C1(C)C=CC=CC=1.CO.ClCCl>[CH3:2][O:6][C:7]1[C:12]2[CH:13]=[CH:14][CH:15]=[CH:16][C:11]=2[O:10][C:9](=[O:17])[C:8]=1[C:18](=[O:33])[CH:19]=[CH:20][C:21]1[CH:26]=[CH:25][CH:24]=[C:23]([NH:27][C:28](=[O:32])[CH2:29][O:30][CH3:31])[CH:22]=1

Komponenten

8

Edukt 4

HCID 8028TetrahydrofuranHCID 11776TriphenylphosphineHCID 220568ethyl N-ethoxycarbonyliminocarbamateHCID 761683104-hydroxy-3-[3-[3-(methoxyacetylamino)phenyl]-1-oxo-2-propenyl]-2H-1-benzopyran-2-one

Produkt 1

HCID 740200054-methoxy-3-[3-[3-(methoxyacetylamino)phenyl]-1-oxo-2-propenyl]-2H-1-benzopyran-2-one

Reagenzien, Katalysatoren, Lösungsmittel 3

HCID 887MethanolLösungsmittelHCID 1140TolueneLösungsmittelHCID 6344DichloromethaneLösungsmittel

Versuchsvorschrift

To a mixture of 5 ml of tetrahydrofuran and 6 ml of dichloromethane were added 0.59 g of 4-hydroxy-3-[3-[3-(methoxyacetylamino)phenyl]-1-oxo-2-propenyl]-2H-1-benzopyran-2-one, 0.45 g of triphenylphosphine and 55 mg of methanol, and to the mixture was added dropwise 0.74 g of a 40% toluene solution of diethyl azodicarboxylate. The mixture was stirred at room temperature for 40 minutes, and the reaction mixture was concentrated under reduced pressure. The residue was subjected to silica gel column chromatography to obtain 0.18 g of 4-methoxy-3-[3-[3-(methoxyacetylamino)phenyl]-1-oxo-2-propenyl]-2H-1-benzopyran-2-one [Compound No. (22d)].

Aufarbeitung

  1. concentrationthe reaction mixture was concentrated under reduced pressure

Quellen und Nachweise

ORD-Eintrag
ord-c3ef72fda628464293ddb6a778e9f6bb
Quelldatensatz
uspto-grants-2010_04
Patentnummer
US07691883B2

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