Ethyl 4-phenylbenzoylformate → 5-[(1,1'-biphenyl)-4-yl]-4-hydroxy-3-phenylmethoxy-5-phenyl-2(5H)-furanone

HRID 369147Notes

Reaction equation

HRID 369147 reaction equation
[C:1]1([Mg]Br)[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=1.C1([C:15]2[CH:27]=[CH:26][C:18]([C:19](C(OCC)=O)=O)=[CH:17][CH:16]=2)C=CC=CC=1.[OH:28][C:29]1[C:30](=[O:42])[O:31][C:32]([CH3:41])([C:35]2[CH:40]=[CH:39][CH:38]=[CH:37][CH:36]=2)[C:33]=1[OH:34]>C1COCC1>[C:38]1([C:1]2[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=2)[CH:39]=[CH:40][C:35]([C:32]2([C:41]3[CH:5]=[CH:6][CH:1]=[CH:2][CH:3]=3)[O:31][C:30](=[O:42])[C:29]([O:28][CH2:19][C:18]3[CH:17]=[CH:16][CH:15]=[CH:27][CH:26]=3)=[C:33]2[OH:34])=[CH:36][CH:37]=1

Participants

5

Reactant 3

HCID 80389Ethyl 4-phenylbenzoylformateHCID 547254993,4-dihydroxy-5-methyl-5-phenyl-2(5H)-furanoneHCID 178418255HCID 178418255, compound

Product 1

HCID 547235905-[(1,1'-biphenyl)-4-yl]-4-hydroxy-3-phenylmethoxy-5-phenyl-2(5H)-furanoneYield 20%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

A total of 3.4 mL (10.2 mmol) of 3.0M phenylmagnesium bromide was added to a solution of 2.4 g (10 mmol) of ethyl 4-phenylbenzoylformate in THF in an analogous manner as described for the synthesis of 3,4-dihydroxy-5-methyl-5-phenyl-2(5H)-furanone to give prior to hydrogenolysis 0.88 g (20% yield) of 5-[(1,1'-biphenyl)-4-yl]-4-hydroxy-3-phenylmethoxy-5-phenyl-2(5H)-furanone as an off white solid: mp 190-195° C. (CHCl3 /hexanes).

Workup

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Sources & evidence

ORD record
ord-c248f55b55b84f4aaf171965e60ca8b0
Source dataset
uspto-grants-2000_10
Patent number
US06136832

Reaction notes

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