4-Hydroxybiphenyl → 5-[2-((1,1'-biphenyl)-4-oxy)ethyl]-3,4-dihydroxy-2(5H)-furanone

HRID 369165Notes

Reaction equation

HRID 369165 reaction equation
[OH:1][C:2]1[CH:7]=[CH:6][C:5]([C:8]2[CH:13]=[CH:12][CH:11]=[CH:10][CH:9]=2)=[CH:4][CH:3]=1.C([O:21][C:22]1[C:23](=[O:38])[O:24][CH:25]([CH2:35][CH2:36]O)[C:26]=1[O:27]CC1C=CC=CC=1)C1C=CC=CC=1>CCOCC>[C:5]1([C:8]2[CH:13]=[CH:12][CH:11]=[CH:10][CH:9]=2)[CH:4]=[CH:3][C:2]([O:1][CH2:36][CH2:35][CH:25]2[O:24][C:23](=[O:38])[C:22]([OH:21])=[C:26]2[OH:27])=[CH:7][CH:6]=1

Participants

4

Reactant 2

HCID 71034-HydroxybiphenylHCID 211841063,4-dibenzyloxy-5-(2-hydroxyethyl)-2(5H)-furanone

Product 1

HCID 699413455-[2-((1,1'-biphenyl)-4-oxy)ethyl]-3,4-dihydroxy-2(5H)-furanoneYield 32%

Reagents, catalysts & solvents 1

HCID 3283Diethyl EtherSolvent

Procedure

Mitsunoble coupling of 0.20 g (1.2 mmol) of 4-hydroxy-1,1'-biphenyl with 0.34 g (1.0 mmol) of 3,4-dibenzyloxy-5-(2-hydroxyethyl)-2(5H)-furanone and subsequent benzyl group deprotection by hydrogenation were performed in a similar manner as described in the synthesis of 3,4-dihydroxy-5-[2-(4-phenoxy)phenoxyethyl]-2(5H)-furanone to provide 100 mg (32% yield) of 5-[2-((1,1'-biphenyl)-4-oxy)ethyl]-3,4-dihydroxy-2(5H)-furanone as a white powder after trituration with ether and hexanes: 1H NMR (acetone-d6) δ 7.71-7.02 (m, 9H), 4.97 (dd, J=4.9, 8.7 Hz, 1H), 4.25 (dd, J=2.6, 4.7 Hz, 2H), 2.58-2.41 (m, 1H), 2.10-1.92 (m, 1H). Anal Calcd for C18H16O5 +1H2O: C, 67.49; H, 5.66. Found: C, 67.34; H, 5.42.

Sources & evidence

ORD record
ord-f9ab0154487d44a782ea9e99f3506302
Source dataset
uspto-grants-2000_10
Patent number
US06136832

Reaction notes

Loading…