Reaktion #160160

Reaktionsgleichung

methyl 4-sulfanylbenzoate

potassium carbonate

3-iodotetrahydrofuran

→

methyl 4-tetrahydrofuran-3-ylsulfanylbenzoate

Ausbeute 86.0%

Lösungsmittel

DMF

DCM

Reaktionsbedingungen

Aufarbeitung

1. 1
   Filtrationfiltered
2. 2
   Sonstigethe solvent was evaporated under reduced pressure
3. 3
   workup.DISSOLUTIONThe residue was dissolved in DCM (25 mL)
4. 4
   Waschenwashed with water (3×15 mL) and saturated aqueous brine solution (1×15 mL)
5. 5
   TrocknenThe organic layer was dried over sodium sulfate
6. 6
   Filtrationfiltered
7. 7
   Einengenconcentrated in vacuo

Vorschrift

To a suspension of methyl 4-sulfanylbenzoate (0.85 g, 5.05 mmol), potassium carbonate (1.39 g, 10.1 mmol) in DMF (10 mL) at room temperature was added 3-iodotetrahydrofuran (1.00 g, 5.05 mmol). The resulting suspension was stirred for 16 hours. The reaction mixture was diluted with DCM (25 mL), filtered and the solvent was evaporated under reduced pressure. The residue was dissolved in DCM (25 mL) and washed with water (3×15 mL) and saturated aqueous brine solution (1×15 mL). The organic layer was dried over sodium sulfate, filtered and concentrated in vacuo to yield methyl 4-tetrahydrofuran-3-ylsulfanylbenzoate (1.03 g, 86%) as a yellow solid. ESI-MS m/z calc. 238.1. Found 239.3 (M+1)+; Retention time: 1.47 minutes (3 min run); 1H NMR (400 MHz, DMSO) δ 7.91-7.83 (m, 2H), 7.48-7.39 (m, 2H), 4.16-4.08 (m, 2H), 3.91-3.72 (m, 5H), 3.55 (q, J=7.6 Hz, 1H), 2.49-2.35 (m, 1H), 1.86-1.74 (m, 1H).

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