1,4-Butanedithiol → 5-[2-[(4-mercaptobutyl)thio]-2-(3-thienyl)ethyl]-2-methyl-2-phenylfuran-3(2H)-one

HRID 50020

Reaktionsgleichung

Reaktionsgleichung von HRID 50020
[CH3:1][C:2]1([C:15]2[CH:20]=[CH:19][CH:18]=[CH:17][CH:16]=2)[C:6](=[O:7])[CH:5]=[C:4](/[CH:8]=[CH:9]/[C:10]2[CH:14]=[CH:13][S:12][CH:11]=2)[O:3]1.[CH2:21]([SH:26])[CH2:22][CH2:23][CH2:24][SH:25]>>[SH:25][CH2:24][CH2:23][CH2:22][CH2:21][S:26][CH:9]([C:10]1[CH:14]=[CH:13][S:12][CH:11]=1)[CH2:8][C:4]1[O:3][C:2]([CH3:1])([C:15]2[CH:20]=[CH:19][CH:18]=[CH:17][CH:16]=2)[C:6](=[O:7])[CH:5]=1

Komponenten

3

Edukt 2

HCID 791481,4-ButanedithiolHCID 11300541(E)-2-methyl-2-phenyl-5-[2-(3-thienyl)ethenyl]-3(2H)-furanone

Produkt 1

HCID 102946645-[2-[(4-mercaptobutyl)thio]-2-(3-thienyl)ethyl]-2-methyl-2-phenylfuran-3(2H)-one

Versuchsvorschrift

According to the procedure of Method A, Example 1, (E)-2-methyl-2-phenyl-5-[2-(3-thienyl)ethenyl]-3(2H)-furanone was reacted with 1,4-butanedithiol to provide 5-[2-[(4-mercaptobutyl)thio]-2-(3-thienyl)ethyl]-2-methyl-2-phenylfuran-3(2H)-one: 1H NMR (CDCl3) δ1.30 (m, 1H), 1.55-1.70 (broad s with fine structure, 4H) and 1.65 and 1.68 (singlets, 3H), 2.33-2.42 (m, 2H), 2.42-2.55 (m, 2H), 3.06-3.25 (m, 2H), 4.40 (m, 1H), 5.37 and 5.39 (singlets, 1H), 7.05-7.18 (m, 2H), 7.25-7.40 (m, 6H); MS (HR-FAB) m/z 405.1029 (M+H calcd. for C21H25O2S3 405.1017).

Quellen und Nachweise

ORD-Eintrag
ord-4206263457e940eda08efefef237a99c
Quelldatensatz
uspto-grants-2004_03
Patentnummer
US06710078B2

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