Potassium Carbonate → 7-[(Oxiran-2-yl)methoxy]-2H-1-benzopyran-2-one

HRID 1903075Notes

Reaction equation

HRID 1903075 reaction equation
[OH:1][C:2]1[CH:11]=[C:10]2[C:5]([CH:6]=[CH:7][C:8](=[O:12])[O:9]2)=[CH:4][CH:3]=1.[CH2:13]([CH:15]1[O:17][CH2:16]1)Br.C(=O)([O-])[O-].[K+].[K+]>C(C(C)=O)C>[O:17]1[CH2:16][CH:15]1[CH2:13][O:1][C:2]1[CH:11]=[C:10]2[C:5]([CH:6]=[CH:7][C:8](=[O:12])[O:9]2)=[CH:4][CH:3]=1

Participants

5

Reactant 3

HCID 11430Potassium CarbonateHCID 18430EpibromohydrinHCID 5281426Umbelliferone

Product 1

HCID 1697957-[(Oxiran-2-yl)methoxy]-2H-1-benzopyran-2-one

Reagents, catalysts & solvents 1

HCID 6569Methyl Ethyl KetoneSolvent

Procedure

Five grams of 7-(2,3-epoxypropoxy)cumarin obtained by the reaction of 7-hydroxycumarin with epibromohydrin in methyl ethyl ketone in the presence of anhydrous potassium carbonate is heated at reflux for seven hours with 3.1 g of N-carbamoylpiperazine in 100 ml of methanol. After the reaction, methanol is evaporated therefrom in vacuo and the residual crystals are washed with ethyl acetate to give 7.9 g of the product. Hydrochloride recrystallized from a mixture of ethanol and dimethyl formamide melts at 198°-200° C.

Sources & evidence

ORD record
ord-12ac68c51daf48e1841654c589935752
Source dataset
uspto-grants-1984_03
Patent number
US04435397

Reaction notes

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