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

HRID 639744Notes

Reaction equation

HRID 639744 reaction equation
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

Participants

8

Reactant 4

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

Product 1

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

Reagents, catalysts & solvents 3

HCID 887MethanolSolventHCID 1140TolueneSolventHCID 6344DichloromethaneSolvent

Procedure

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)].

Workup

  1. concentrationthe reaction mixture was concentrated under reduced pressure

Sources & evidence

ORD record
ord-c3ef72fda628464293ddb6a778e9f6bb
Source dataset
uspto-grants-2010_04
Patent number
US07691883B2

Reaction notes

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