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

HRID 369146Notes

Reaction equation

HRID 369146 reaction equation
[C:1]1([C:26]2[CH:31]=[CH:30][CH:29]=[CH:28][CH:27]=2)[CH:6]=[CH:5][C:4]([C:7]2([CH2:22][CH:23]([CH3:25])[CH3:24])[O:11][C:10](=[O:12])[C:9]([O:13]CC3C=CC=CC=3)=[C:8]2[OH:21])=[CH:3][CH:2]=1.OC1C(=O)OC(C)(C2C=CC=CC=2)C=1O>>[C:1]1([C:26]2[CH:27]=[CH:28][CH:29]=[CH:30][CH:31]=2)[CH:6]=[CH:5][C:4]([C:7]2([CH2:22][CH:23]([CH3:25])[CH3:24])[O:11][C:10](=[O:12])[C:9]([OH:13])=[C:8]2[OH:21])=[CH:3][CH:2]=1

Participants

3

Reactant 2

HCID 547235955-[(1,1'-biphenyl)-4-yl]-4-hydroxy-3-phenylmethoxy-5-(2-methylpropyl)-2(5H)-furanoneHCID 547254993,4-dihydroxy-5-methyl-5-phenyl-2(5H)-furanone

Product 1

HCID 547254965-[(1,1'-Biphenyl)-4-yl]-3,4-dihydroxy-5-(2-methylpropyl)-2(5H)-furanoneYield 69.4%

Procedure

Hydrogenolysis of 350 mg of 5-[(1,1'-biphenyl)-4-yl]-4-hydroxy-3-phenylmethoxy-5-(2-methylpropyl)-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 190 mg (69% yield) of a white powder: mp 198-199° C. dec.(CHCl3 /hexanes). 1H NMR (acetone-d6) δ 7.73-7.34 (m, 9H), 2.44-2.28 (m, 1H), 1.50-0.80 (m, 8H). 13C NMR (acetone-d6) δ 169.21, 155.47, 140.81, 139.57, 129.17, 127.73, 127.18, 127.08, 126.04, 118.47, 86.01, 40.66, 23.72, 12.11, 11.87. Anal Calcd for C20H20O4 +0.125 H2O: C, 73.55; H, 6.25. Found: C, 73.25; H, 6.36.

Sources & evidence

ORD record
ord-f2f0b4e2ff164e569f6ecd7397832345
Source dataset
uspto-grants-2000_10
Patent number
US06136832

Reaction notes

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