Ethyl 4-iso-butylbenzoylformate → 4-hydroxy-5-(4-isobutylphenyl)-3-phenylmethoxy-5-(1-propyl)-2(5H)-furanone

HRID 369151Notes

Reaction equation

HRID 369151 reaction equation
[CH2:1]([Mg]Br)[CH2:2][CH3:3].[CH2:6]([C:10]1[CH:22]=[CH:21][C:13]([C:14]([C:16]([O:18]CC)=O)=[O:15])=[CH:12][CH:11]=1)[CH:7]([CH3:9])[CH3:8].[OH:23][C:24]1[C:25](=O)[O:26][C:27](C)([C:30]2[CH:35]=[CH:34][CH:33]=[CH:32][CH:31]=2)C=1O>C1COCC1>[OH:18][C:16]1[C:14]([C:13]2[CH:12]=[CH:11][C:10]([CH2:6][CH:7]([CH3:8])[CH3:9])=[CH:22][CH:21]=2)([CH2:1][CH2:2][CH3:3])[O:15][C:24](=[O:23])[C:25]=1[O:26][CH2:27][C:30]1[CH:35]=[CH:34][CH:33]=[CH:32][CH:31]=1

Participants

5

Reactant 3

HCID 12585534Ethyl 4-iso-butylbenzoylformateHCID 547254993,4-dihydroxy-5-methyl-5-phenyl-2(5H)-furanoneHCID 178455851HCID 178455851, compound

Product 1

HCID 702473524-hydroxy-5-(4-isobutylphenyl)-3-phenylmethoxy-5-(1-propyl)-2(5H)-furanone

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

A total of 5.2 mL (10.4 mmol) of 2.0M 1-propylmagnesium bromide was added to a solution of 2.3 g (10 mmol) of ethyl 4-isobutylbenzoylformate in THF in an analogous manner as described for the synthesis of 3,4-dihydroxy-5-methyl-5-phenyl-2(5H)-furanone to provide 4-hydroxy-5-(4-isobutylphenyl)-3-phenylmethoxy-5-(1-propyl)-2(5H)-furanone as an oil, which was purified over SiO2 using acetone/hexanes (1/4).

Sources & evidence

ORD record
ord-95f12095aca7480e82c8c76902c811fe
Source dataset
uspto-grants-2000_10
Patent number
US06136832

Reaction notes

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