3,4-dibenzyloxy-5-(2-hydroxyethyl)-2(5H)-furanone → 3,4-dihydroxy-5-[2-(quinoline-2-oxy)ethyl]-2(5H)-furanone

HRID 369166Notes

Reaction equation

HRID 369166 reaction equation
[OH:1][C:2]1[CH:11]=[CH:10][C:9]2[C:4](=[CH:5][CH:6]=[CH:7][CH:8]=2)[N:3]=1.C([O:19][C:20]1[C:21](=[O:36])[O:22][CH:23]([CH2:33][CH2:34]O)[C:24]=1[O:25]CC1C=CC=CC=1)C1C=CC=CC=1>>[OH:19][C:20]1[C:21](=[O:36])[O:22][CH:23]([CH2:33][CH2:34][O:1][C:2]2[CH:11]=[CH:10][C:9]3[C:4](=[CH:5][CH:6]=[CH:7][CH:8]=3)[N:3]=2)[C:24]=1[OH:25]

Participants

3

Reactant 2

HCID 211841063,4-dibenzyloxy-5-(2-hydroxyethyl)-2(5H)-furanoneHCID 178515546HCID 178515546, compound

Product 1

HCID 699410093,4-dihydroxy-5-[2-(quinoline-2-oxy)ethyl]-2(5H)-furanoneYield 17.4%

Procedure

Mitsunoble coupling of 0.17 g (1.2 mmol) of 2-hydroxyquinoline 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 50 mg (17% yield) of 3,4-dihydroxy-5-[2-(quinoline-2-oxy)ethyl]-2(5H)-furanone as a fluffy white solid after recrystallization from ether and hexanes: 1H NMR (acetone-d6) δ 8.25-8.17 (m, 1H); 7.88-7.38 (m, 4H), 7.01-6.93 (m, 1H); 4.97 (dd, J=4.9, 8.7 H, 1H), 4.81-4.55 (m, 2H); 2.62-2.45 (m, 1H), 2.20-1.95 (m, 1H). Anal Calcd for C15H13NO5 +0.5H2O: C, 60.81; H, 5.10; N, 4.72. Found: C, 61.04; H 5.04: N, 4.32.

Sources & evidence

ORD record
ord-9e2eb5c3209a43aaa2cdbb7312c7e276
Source dataset
uspto-grants-2000_10
Patent number
US06136832

Reaction notes

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