Potassium Carbonate → HCID 21842558, compound

HRID 1737291Notes

Reaction equation

HRID 1737291 reaction equation
[OH:1][C:2]1[C:11]2[C:6](=[CH:7][CH:8]=[CH:9][CH:10]=2)OC(=O)[CH:3]=1.O[C:14]1[CH:23]=[C:22]2[C:17]([CH:18]=[CH:19][C:20](=[O:24])[O:21]2)=[CH:16][CH:15]=1.[OH:25]C1C=C2C(C(C)=CC(=O)O2)=CC=1.ClC1C(=O)OC2C(C=1C)=CC=C(O)C=2.OC1C(C)=C2C(C(C)=C(C)C(=O)O2)=CC=1.C(=O)([O-])[O-].[K+].[K+]>CC(C)=O>[O:1]=[C:2]([C:11]1[CH:10]=[CH:9][CH:8]=[CH:7][CH:6]=1)[CH2:3][O:25][C:19]1[C:20](=[O:24])[O:21][C:22]2[CH:23]=[CH:14][CH:15]=[CH:16][C:17]=2[CH:18]=1

Participants

8

Reactant 6

HCID 11430Potassium CarbonateHCID 52805674-MethylumbelliferoneHCID 5281426UmbelliferoneHCID 53550793-Chloro-7-hydroxy-4-methyl-2-benzopyroneHCID 53971957-Hydroxy-3,4,8-trimethylcoumarinHCID 546829304-Hydroxycoumarin

Product 1

HCID 21842558HCID 21842558, compound

Reagents, catalysts & solvents 1

HCID 180AcetoneSolvent

Procedure

Each of the commercially available 4-hydroxycoumarin, 7-hydroxycoumarin(R3 =R4 =R5 =H), 7-hydroxy-4-methylcoumarin(R4 =CH3), 3-chloro-7-hydroxy-4-methylcoumarin(R3 =Cl, R4 =CH3), and 7-hydroxy-3,4,8-trimethylcoumarin (R3 =R4 =R5 =CH3) was treated with potassium carbonate and a haloketone (chloroacetone, R1 =CH3 ; 2-bromoacetophenone, R1 =C6H5 ; 2-bromo-4'-fluoroacetophenone, R1 =C6H4F; 2-bromo-4'-chloroacetophenone, R1 =C6H4Cl; 2-bromo-4'-bromoacetophenone, R1 =C6H4Br; 2-bromo-4'-iodoacetophenone, R1 =C6H4I; 2-bromo-4'-methylacetophenone, R1 =C6H4CH3 ; 2-bromo-4'-nitroacetophenone, R1 =C6H4NO2 ; 2-bromo-4'-methoxyacetophenone, R1 =C6H4OCH3 ; 2-bromo-4'-phenylacetophenone, R1 =C6H4C6H5) in acetone to provide (2-oxo-2-phenyl ethoxy)-2H-1-benzopyran-2-one which was reacted with ethyl 2-(bromomethyl)acrylate in tetrahydrofuran(THF) (Reformatsky reaction) to produce 4-[(2,3,4,5-tetrahydro-3-methylene-2-oxo-5-furanyl)methoxy]-2H-1-benzopyran-2-ones and 7-[(2,3,4,5-tetrahydro-3-methylene-2-oxo-5-furanyl)-methoxy]-2H-1-benzopyran-2-ones as shown in Scheme 2.

Sources & evidence

ORD record
ord-ffbe009fa0614f548505b608703c7323
Source dataset
uspto-grants-1999_10
Patent number
US05962460

Reaction notes

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