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

HRID 369143Notes

Reaction equation

HRID 369143 reaction equation
[CH2:1]([Mg]Br)[CH2:2][CH3:3].[C:6]1([C:12]2[CH:24]=[CH:23][C:15]([C:16]([C:18]([O:20]CC)=O)=[O:17])=[CH:14][CH:13]=2)[CH:11]=[CH:10][CH:9]=[CH:8][CH:7]=1.[OH:25][C:26]1[C:27](=O)[O:28][C:29](C)([C:32]2[CH:37]=[CH:36][CH:35]=[CH:34][CH:33]=2)C=1O.C(Cl)(Cl)Cl>C1COCC1>[C:12]1([C:6]2[CH:7]=[CH:8][CH:9]=[CH:10][CH:11]=2)[CH:13]=[CH:14][C:15]([C:16]2([CH2:1][CH2:2][CH3:3])[O:17][C:26](=[O:25])[C:27]([O:28][CH2:29][C:32]3[CH:33]=[CH:34][CH:35]=[CH:36][CH:37]=3)=[C:18]2[OH:20])=[CH:23][CH:24]=1

Participants

6

Reactant 4

HCID 6212ChloroformHCID 80389Ethyl 4-phenylbenzoylformateHCID 547254993,4-dihydroxy-5-methyl-5-phenyl-2(5H)-furanoneHCID 178455851HCID 178455851, compound

Product 1

HCID 547236025-[(1,1'-biphenyl)-4-yl]-4-hydroxy-3-phenylmethoxy-5-propyl-2(5H)-furanoneYield 8%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

A total of 5.2 mL (10.4 mmol) of 2.0M n-propylmagnesium 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 0.30 g (8% yield) of 5-[(1,1'-biphenyl)-4-yl]-4-hydroxy-3-phenylmethoxy-5-propyl-2(5H)-furanone as an off white solid after crystallization from CHCl3 and hexanes.

Workup

  1. customto give

Sources & evidence

ORD record
ord-f61444d242b0494bbc8fddf7b7ed6886
Source dataset
uspto-grants-2000_10
Patent number
US06136832

Reaction notes

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