Ethanol → HCID 131720095, compound

HRID 265631Notes

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.C(N(CC)CC)C.[CH2:51]([OH:53])[CH3:52]>>[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:53][CH2:51][CH2:52][S:43][C:40]1[CH:41]=[CH:42][C:37]([Cl:36])=[CH:38][CH:39]=1

Participants

Reactant 4

HCID 702Ethanol

HCID 7815p-Chlorothiophenol

HCID 8471Triethylamine

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 triethylamine (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-3b14191991a743baa68ad08dbfc5d352
Source dataset: uspto-grants-1997_07
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US05648486

Reaction notes

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