Chloroform → 5-[(1,1'-biphenyl)-4-yl]-4-hydroxy-3-phenylmethoxy-5-(2-methylpropyl)-2(5H)-furanone

HRID 612555Notes

Reaction equation

HRID 612555 reaction equation
[CH2:1]([Mg]Br)[CH:2]([CH3:4])[CH3:3].[C:7]1([C:13]2[CH:25]=[CH:24][C:16]([C:17]([C:19]([O:21]CC)=O)=[O:18])=[CH:15][CH:14]=2)[CH:12]=[CH:11][CH:10]=[CH:9][CH:8]=1.[OH:26][C:27]1[C:28](=O)[O:29][C:30](C)([C:33]2[CH:38]=[CH:37][CH:36]=[CH:35][CH:34]=2)C=1O.C(Cl)(Cl)Cl>C1COCC1>[C:13]1([C:7]2[CH:8]=[CH:9][CH:10]=[CH:11][CH:12]=2)[CH:14]=[CH:15][C:16]([C:17]2([CH2:1][CH:2]([CH3:4])[CH3:3])[O:18][C:27](=[O:26])[C:28]([O:29][CH2:30][C:33]3[CH:34]=[CH:35][CH:36]=[CH:37][CH:38]=3)=[C:19]2[OH:21])=[CH:24][CH:25]=1

Participants

6

Reactant 4

HCID 6212ChloroformHCID 80389Ethyl 4-phenylbenzoylformateHCID 547254993,4-dihydroxy-5-methyl-5-phenyl-2(5H)-furanoneHCID 178418816HCID 178418816, compound

Product 1

HCID 547235955-[(1,1'-biphenyl)-4-yl]-4-hydroxy-3-phenylmethoxy-5-(2-methylpropyl)-2(5H)-furanoneYield 8%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

A total of 5.2 mL (10.4 mmol) of 2.0 M isobutylmagnesium 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 0.35 g (8% yield) of 5-[(1,1'-biphenyl)-4-yl]-4-hydroxy-3-phenylmethoxy-5-(2-methylpropyl)-2(5H)-furanone as an off white solid after crystallization from CHCl3 and hexanes.

Workup

  1. customto give

Sources & evidence

ORD record
ord-be61d16b49c44bd1aa0e582dbb4ca2a6
Source dataset
uspto-grants-1999_12
Patent number
US06005000

Reaction notes

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