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

HRID 369139Notes

Reaction equation

HRID 369139 reaction equation
[C:1]1([C:23]2[CH:28]=[CH:27][CH:26]=[CH:25][CH:24]=2)[CH:6]=[CH:5][C:4]([C:7]2([CH3:22])[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:23]2[CH:24]=[CH:25][CH:26]=[CH:27][CH:28]=2)[CH:6]=[CH:5][C:4]([C:7]2([CH3:22])[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 547187555-[(1,1'-biphenyl)-4-yl]-3-phenylmethoxy-4-hydroxy-5-methyl-2(5H)-furanoneHCID 547254993,4-dihydroxy-5-methyl-5-phenyl-2(5H)-furanone

Product 1

HCID 546844825-[(1,1'-biphenyl)-4-yl]-3,4-dihydroxy-5-methyl-2(5H)-furanoneYield 63.3%

Procedure

Hydrogenolysis of 500 mg of the 5-[(1,1'-biphenyl)-4-yl]-3-phenylmethoxy-4-hydroxy-5-methyl-2(5H)-furanone was performed in a similar manner as described in the synthesis of 3,4-dihydroxy-5-methyl-5-phenyl-2(5H)-furanone to provided 240 mg (63% yield) of 5-[(1,1'-biphenyl)-4-yl]-3,4-dihydroxy-5-methyl-2(5H)-furanone as a white powder: mp 206-212° C. dec. (MeOH/H2O), 1H NMR (acetone-d6) δ 7.69-7.33 (m, 9H), 1.88 (s, 3H). 13C NMR (acetone-d6) δ 169.5, 157.1, 141.6, 141.0, 139.8, 129.6, 128.3, 127.6, 127.6, 126.6, 117.9, 81.2, 24.5. Anal Calcd for C17H14O4 : C, 72.33; H, 5.00. Found: C, 72.07; H, 5.14.

Sources & evidence

ORD record
ord-8c6aeee898f542c8bd8567974873b143
Source dataset
uspto-grants-2000_10
Patent number
US06136832

Reaction notes

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