1,3-Propanedithiol → 5-[2-[(3-mercaptopropyl)thio]-2-(3-thienyl)ethyl]-2-methyl-2-phenylfuran-3(2H)-one

HRID 50022

Reaction equation

HRID 50022 reaction equation
[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:25])[CH2:22][CH2:23][SH:24]>>[SH:24][CH2:23][CH2:22][CH2:21][S:25][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

Participants

3

Reactant 2

HCID 80131,3-PropanedithiolHCID 11300541(E)-2-methyl-2-phenyl-5-[2-(3-thienyl)ethenyl]-3(2H)-furanone

Product 1

HCID 101572355-[2-[(3-mercaptopropyl)thio]-2-(3-thienyl)ethyl]-2-methyl-2-phenylfuran-3(2H)-one

Procedure

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 1,3-propanedithiol to provide 5-[2-[(3-mercaptopropyl)thio]-2-(3-thienyl)ethyl]-2-methyl-2-phenylfuran-3(2H)-one: 1H NMR (CDCl3) δ1.65 and 1.68 (singlets, 3H), 2.41 (m, 2H), 1.73-2.20 (overlapping multiplets, 3H), 2.45-2.65 (m, ˜4H) 3.08-3.27 (m, 2H), 4.40 (m, 1H), 5.37 and 5.39 (singlets, 1H), 7.05-7.18 (m, 2H), 7.27-7.45 (m, 6H); MS (HR-FAB) m/z 391.0850 (M+H calcd. for C20H23O2S3 391.0860).

Sources & evidence

ORD record
ord-4cf5fa8f8dd543b6b178b61fe289611c
Source dataset
uspto-grants-2004_03
Patent number
US06710078B2

Linked notes

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