Thioglycerol → 5-[2-[(2,3-dihydroxypropyl)thio]-2-(3-thienyl)ethyl]-2-methyl-2-phenylfuran-3(2H)-one

HRID 50027

Reaction equation

HRID 50027 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.[SH:21][CH2:22][CH:23]([OH:26])[CH2:24][OH:25]>>[OH:26][CH:23]([CH2:24][OH:25])[CH2:22][S:21][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 7291ThioglycerolHCID 11300541(E)-2-methyl-2-phenyl-5-[2-(3-thienyl)ethenyl]-3(2H)-furanone

Product 1

HCID 102937885-[2-[(2,3-dihydroxypropyl)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 3-mercapto-1,2-propanediol to provide 5-[2-[(2,3-dihydroxypropyl)thio]-2-(3-thienyl)ethyl]-2-methyl-2-phenylfuran-3(2H)-one; 1H NMR (CDCl3) δ1.66 and 1.68 (singlets, 3H), 1.83 (br s, 1H), 2.44 (br s with fine structure, 1H) and overlapping 2.45-2.58 (m, 2H), 3.10-3.28 (m, 2H), 3.47 (br s with fine structure, 1H), 3.55-3.78 (m, 2H), 4.50 (m, 1H), 5.39 and 5.40 (overlapping singlets, 1H), 7.05-7.20 (m, 2H), 7.27-7.43 (m, 6H); MS (HR-EI) m/z 390.0948 (M+ calcd. for C20H22O4S2 390.0959).

Sources & evidence

ORD record
ord-c084fb6ec1b84e428e9b3243aff81748
Source dataset
uspto-grants-2004_03
Patent number
US06710078B2

Linked notes

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