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

HRID 369144Notes

Reaction equation

HRID 369144 reaction equation
[C:1]1([C:25]2[CH:30]=[CH:29][CH:28]=[CH:27][CH:26]=2)[CH:6]=[CH:5][C:4]([C:7]2([CH2:22][CH2:23][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:25]2[CH:26]=[CH:27][CH:28]=[CH:29][CH:30]=2)[CH:6]=[CH:5][C:4]([C:7]2([CH2:22][CH2:23][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 547236025-[(1,1'-biphenyl)-4-yl]-4-hydroxy-3-phenylmethoxy-5-propyl-2(5H)-furanoneHCID 547254993,4-dihydroxy-5-methyl-5-phenyl-2(5H)-furanone

Product 1

HCID 547255015-[(1,1'-Biphenyl)-4-yl]-3,4-dihydroxy-5-propyl-2(5H)-furanoneYield 52%

Procedure

Hydrogenolysis of 250 mg of 5-[(1,1'-biphenyl)-4-yl]-4-hydroxy-3-phenylmethoxy-5-propyl-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 provided 100 mg (52% yield) of a white powder: mp 203-204° C. dec.(acetone/CHCl3 /hexanes). 1H NMR (acetone-d6) δ 7.65-7.40 (m, 9H), 2.25-1.95 (m, 2H), 1.45-1.10 (m, 2H), 0.95 (t, J=6.9 Hz, 3H). Anal Calcd for C19H18O4 +0.125 H2O: C, 73.01; H, 5.88. Found: C, 72.99; H, 5.86.

Sources & evidence

ORD record
ord-961745056fd8451b9a5c1ce10f4abd08
Source dataset
uspto-grants-2000_10
Patent number
US06136832

Reaction notes

Loading…