Potassium Carbonate → 7-(1-ethoxy-carbonylethyl)oxy-3-(4-hydroxyphenyl)-4H-1-benzopyran-4-one

HRID 236342

Reaction equation

[OH:1][C:2]1[CH:19]=[CH:18][C:5]2[C:6](=[O:17])[C:7]([C:10]3[CH:15]=[CH:14][C:13]([OH:16])=[CH:12][CH:11]=3)=[CH:8][O:9][C:4]=2[CH:3]=1.Br[CH:21]([CH3:27])[C:22]([O:24][CH2:25][CH3:26])=O.C(=O)([O-])[O-:29].[K+].[K+]>CN(C)C=O>[CH2:25]([O:24][CH:22]([O:1][C:2]1[CH:19]=[CH:18][C:5]2[C:6](=[O:17])[C:7]([C:10]3[CH:11]=[CH:12][C:13]([OH:16])=[CH:14][CH:15]=3)=[CH:8][O:9][C:4]=2[CH:3]=1)[CH:21]=[C:27]=[O:29])[CH3:26]

Participants

Conditions

Temperature: 80 °C

Procedure

A mixture of 4.0 g of 7-hydroxy-3-(4-hydroxyphenyl)-4H-1-benzopyran-4-one, 3.42 g of ethyl 2-bromopropionate, 60 ml of dimethylformamide and 4.3 g of potassium carbonate was stirred well with heating at 80° C. for 2 hours, poured into ice water and extracted with ethyl acetate. The extract was washed with water and concentrated and the residue was recrystallized from dichloroethane to give 3.0 g of 7-(1-ethoxy- carbonylethyl)oxy-3-(4-hydroxyphenyl)-4H-1-benzopyran-4-one as white crystals. m.p. 172°-173° C.

Workup

extractionextracted with ethyl acetate
washThe extract was washed with water
concentrationconcentrated
customthe residue was recrystallized from dichloroethane

Sources & evidence

ORD record: ord-122f3f1eb7e848a48d97ae0877aab56c
Source dataset: uspto-grants-1987_02
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US04644012

Linked notes

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