Ethyl benzoylformate → HCID 54723598, compound

HRID 369149Notes

Reaction equation

HRID 369149 reaction equation
[C:1]1([Mg]Br)[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=1.[C:9]([C:17]([O:19]CC)=O)(=[O:16])[C:10]1[CH:15]=[CH:14][CH:13]=[CH:12][CH:11]=1.[OH:22][C:23]1[C:24](=O)[O:25][C:26](C)([C:29]2[CH:34]=[CH:33][CH:32]=[CH:31][CH:30]=2)C=1O>C1COCC1>[C:1]1([C:9]2([C:10]3[CH:11]=[CH:12][CH:13]=[CH:14][CH:15]=3)[O:16][C:23](=[O:22])[C:24]([O:25][CH2:26][C:29]3[CH:34]=[CH:33][CH:32]=[CH:31][CH:30]=3)=[C:17]2[OH:19])[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=1

Participants

5

Reactant 3

HCID 15349Ethyl benzoylformateHCID 547254993,4-dihydroxy-5-methyl-5-phenyl-2(5H)-furanoneHCID 178418255HCID 178418255, compound

Product 1

HCID 54723598HCID 54723598, compound

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

A total of 3.5 mL (10.5 mmol) of 3.0M phenylmagnesium bromide was added to a solution of 1.6 mL (10 mmol) of ethyl benzoylformate in THF in an analogous manner as described for the synthesis of 3,4-dihydroxy-5-methyl-5-phenyl-2(5H)-furanone to give 5,5-diphenyl-4-hydroxy-3-phenylmethoxy-2(5H)-furanone as an oil, which was purified over SiO2 using acetone/hexanes (3/7).

Sources & evidence

ORD record
ord-bf6c47297c4543c3b90e874dd5b2245b
Source dataset
uspto-grants-2000_10
Patent number
US06136832

Reaction notes

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