Ethanol → HCID 131720095, compound

HRID 1597408Notes

Reaction equation

[CH3:1][O:2][C:3]1[C:4](OCCOS(O)(=O)=O)=[C:5]([C@H:11]2[CH2:15][CH2:14][C@H:13]([C:16]3[CH:21]=[C:20]([O:22][CH3:23])[C:19]([O:24][CH3:25])=[C:18]([O:26][CH3:27])[CH:17]=3)[O:12]2)[CH:6]=[C:7]([I:10])[C:8]=1C.[Cl:36][C:37]1[CH:42]=[CH:41][C:40]([SH:43])=[CH:39][CH:38]=1.CN(C)C.[CH2:48]([OH:50])[CH3:49]>>[CH3:1][O:2][C:3]1[CH:4]=[C:5]([C@H:11]2[CH2:15][CH2:14][C@H:13]([C:16]3[CH:21]=[C:20]([O:22][CH3:23])[C:19]([O:24][CH3:25])=[C:18]([O:26][CH3:27])[CH:17]=3)[O:12]2)[CH:6]=[C:7]([I:10])[C:8]=1[O:50][CH2:48][CH2:49][S:43][C:40]1[CH:41]=[CH:42][C:37]([Cl:36])=[CH:38][CH:39]=1

Participants

Reactant 4

HCID 702Ethanol

HCID 1146Trimethylamine

HCID 7815p-Chlorothiophenol

HCID 131720096HCID 131720096, compound

Product 1

HCID 131720095HCID 131720095, compound

Procedure

trans-2-(3-Methoxy-4-methylsulfoxyethoxy-5-iodophenyl)-5-(3,4,5-trimethoxyphenyl)tetrahydrofuran (2.5 g, 4.11 mmol) was dissolved in 50 mL ethanol. To this solution was added 4-chlorothiophenol (1.19 g, 8.22 mmol) and trimethylamine (0.831 g, 8.22 mmol). The reaction mixture was refluxed for 16 hours and then the solvent was removed in vacuo. The residue was purified by column chromatography (silica, 3:1 hexane/ethyl acetate)(2.35 g, 87%). 1H NMR (CDCl3): 1.97 (m, 2H); 2.45 (m, 2H); 3.35 (t, 2H); 3.82 (s, 3H); 3.84 (s, 3H), 3.88 (s, 6H); 4.11 (t, 2H); 5.17 (m, 2H), 6.61 (s, 2H); 6.92 (s, 1H); 7.26 (d, 2H); 7.33 (d, 2H); 7.35 (s, 1H).

Workup

temperatureThe reaction mixture was refluxed for 16 hours
customthe solvent was removed in vacuo
customThe residue was purified by column chromatography (silica, 3:1 hexane/ethyl acetate)(2.35 g, 87%)

Sources & evidence

ORD record: ord-d6293e0d469742e78d236903370cd854
Source dataset: uspto-grants-2001_09
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US06294574B1

Reaction notes

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