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

HRID 369138Notes

Reaction equation

HRID 369138 reaction equation
[CH3:1][Mg]I.[C:4]1([C:10]2[CH:22]=[CH:21][C:13]([C:14]([C:16]([O:18]CC)=O)=[O:15])=[CH:12][CH:11]=2)[CH:9]=[CH:8][CH:7]=[CH:6][CH:5]=1.[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>[C:10]1([C:4]2[CH:5]=[CH:6][CH:7]=[CH:8][CH:9]=2)[CH:11]=[CH:12][C:13]([C:14]2([CH3:1])[O:15][C:24](=[O:23])[C:25]([O:26][CH2:27][C:30]3[CH:35]=[CH:34][CH:33]=[CH:32][CH:31]=3)=[C:16]2[OH:18])=[CH:21][CH:22]=1

Participants

5

Reactant 3

HCID 80389Ethyl 4-phenylbenzoylformateHCID 547254993,4-dihydroxy-5-methyl-5-phenyl-2(5H)-furanoneHCID 178418373HCID 178418373, compound

Product 1

HCID 547187555-[(1,1'-biphenyl)-4-yl]-3-phenylmethoxy-4-hydroxy-5-methyl-2(5H)-furanoneYield 30%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent2×

Procedure

A total of 3.4 mL (10.2 mmol) of 3.0M methylmagnesium iodide in THF was added to a THF solution of 2.4 g (10 mmol) of ethyl 4-phenylbenzoylformate 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, 1.1 g (30% yield) of 5-[(1,1'-biphenyl)-4-yl]-3-phenylmethoxy-4-hydroxy-5-methyl-2(5H)-furanone as a white granular solid: m.p. 182-183° C. (benzene/hexanes) 1H NMR (CDCl3) δ 7.56-7.26 (m, 14H), 5.10 (ab quartet, 2H, J=11.4 Hz), 1.79 (s, 3H). 13C NMR (CDCl3) δ 168.5, 163.8, 141.5, 140.3, 137.0, 136.3, 129.0, 128.8, 128.8, 128.8, 127.6, 127.2, 127.1, 125.6, 119.0, 81.1, 73.5, 24.3. Anal Calcd for C24H20O4 : C, 77.40; H, 5.41. Found: C, 77.99; H, 5.61.

Workup

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Sources & evidence

ORD record
ord-3d210714a17d42dc937fc632dfedec31
Source dataset
uspto-grants-2000_10
Patent number
US06136832

Reaction notes

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