HCID 54723598, compound → HCID 54705086, compound

HRID 1385015Notes

Reaction equation

HRID 1385015 reaction equation
[C:1]1([C:7]2([C:22]3[CH:27]=[CH:26][CH:25]=[CH:24][CH:23]=3)[O:11][C:10](=[O:12])[C:9]([O:13]CC3C=CC=CC=3)=[C:8]2[OH:21])[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=1.OC1C(=O)OC(C)(C2C=CC=CC=2)C=1O>>[OH:13][C:9]1[C:10](=[O:12])[O:11][C:7]([C:22]2[CH:23]=[CH:24][CH:25]=[CH:26][CH:27]=2)([C:1]2[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=2)[C:8]=1[OH:21]

Participants

3

Reactant 2

HCID 54723598HCID 54723598, compoundHCID 547254993,4-dihydroxy-5-methyl-5-phenyl-2(5H)-furanone

Product 1

HCID 54705086HCID 54705086, compoundYield 5.6%

Procedure

Hydrogenolysis of 5,5-diphenyl-4-hydroxy-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 150 mg (5.6% overall yield) of 3,4-dihydroxy-5,5-diphenyl-2(5H)-furanone as colorless needles: mp 192-193° C. dec.(CHCl3/hexanes). 1H NMR (acetone-d6) δ 7.41 (s, 10H). 13C NMR (acetone-d6) δ 168.38, 154.92, 140.44, 128.72, 128.58, 127.43, 119.46, 84.74. Anal Calcd for C16H12O4+0.25 H2O C, 70.46; H, 4.62. Found: C, 70.42; H, 4.52.

Sources & evidence

ORD record
ord-49b1885d62c64e77b03bce555e3668e7
Source dataset
uspto-grants-2001_07
Patent number
US06262073B1

Reaction notes

Loading…