4-hydroxy-5-(4-isobutylphenyl)-5-phenyl-3-phenylmethoxy-2(5H)-furanone → 3,4-dihydroxy-5-(4-isobutylphenyl)-5-phenyl-2(5H)-furanone

HRID 369154Notes

Reaction equation

HRID 369154 reaction equation
[OH:1][C:2]1[C:6]([C:13]2[CH:18]=[CH:17][C:16]([CH2:19][CH:20]([CH3:22])[CH3:21])=[CH:15][CH:14]=2)([C:7]2[CH:12]=[CH:11][CH:10]=[CH:9][CH:8]=2)[O:5][C:4](=[O:23])[C:3]=1[O:24]CC1C=CC=CC=1.OC1C(=O)OC(C)(C2C=CC=CC=2)C=1O>>[OH:24][C:3]1[C:4](=[O:23])[O:5][C:6]([C:13]2[CH:14]=[CH:15][C:16]([CH2:19][CH:20]([CH3:21])[CH3:22])=[CH:17][CH:18]=2)([C:7]2[CH:12]=[CH:11][CH:10]=[CH:9][CH:8]=2)[C:2]=1[OH:1]

Participants

3

Reactant 2

HCID 547235924-hydroxy-5-(4-isobutylphenyl)-5-phenyl-3-phenylmethoxy-2(5H)-furanoneHCID 547254993,4-dihydroxy-5-methyl-5-phenyl-2(5H)-furanone

Product 1

HCID 547254973,4-dihydroxy-5-(4-isobutylphenyl)-5-phenyl-2(5H)-furanoneYield 51.4%

Procedure

Hydrogenolysis of 500 mg (1.2 mmol) of 4-hydroxy-5-(4-isobutylphenyl)-5-phenyl-3-phenylmethoxy-2(5H)-furanone was performed in a similar manner as described in the preparation of 3,4-dihydroxy-5-methyl-5-phenyl-2(5H)-furanone to provide 200 mg (51% yield) of 3,4-dihydroxy-5-(4-isobutylphenyl)-5-phenyl-2(5H)-furanone as a white powder: mp 138-139° C. (CHCl3 /hexanes). 1H NMR (acetone-d6) δ 7.40-7.15 (m, 9H), 2.49 (d, J=7.1 Hz, 2H), 1.94-1.74 (m, 1H), 0.89 (d, J=6.5 Hz, 6H). Anal Calcd for C20H20O4 : C, 74.1; H, 6.2. Found: C, 73.7; H, 6.3.

Sources & evidence

ORD record
ord-60a2e17287284c32959b54cb755835b9
Source dataset
uspto-grants-2000_10
Patent number
US06136832

Reaction notes

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