Reaktion #91008

Reaktionsgleichung

methyl 3-chloro-4,5-dihydroxybenzoate

Methyl 3-chloro-4,5-dihydroxybenzoate

iodocyclopentane

potassium carbonate

→

methyl 3-chloro-4,5-bis(cyclopentyloxy)benzoate

Ausbeute 85.1%

Methyl 3-chloro-4,5-bis(cyclopentyloxy)benzoate

Ausbeute 85.1%

Lösungsmittel

DMF

Reaktionsbedingungen

Aufarbeitung

1. 1
   TemperaturThe reaction mixture was cooled to room temperature
2. 2
   Sonstigepartitioned between 1M HCl (75 mL) and EtOAc (100 mL)
3. 3
   SonstigeThe phases were separated
4. 4
   Waschenthe organic phase was washed with brine (2×75 mL)
5. 5
   Trocknenthen dried over MgSO4
6. 6
   Filtrationfiltered
7. 7
   SonstigeThe solvent was removed in vacuo
8. 8
   Sonstigethe residue was purified by silica gel chromatography (40 g, 0-100% EtOAc in isohexane)

Vorschrift

A mixture of methyl 3-chloro-4,5-dihydroxybenzoate (3) (300 mg, 1.48 mmol), iodocyclopentane (558 μL, 4.44 mmol) and potassium carbonate (614 mg, 4.44 mmol) in DMF (10 mL) was stirred at 70° C. for 46 h. The reaction mixture was cooled to room temperature and then partitioned between 1M HCl (75 mL) and EtOAc (100 mL). The phases were separated and the organic phase was washed with brine (2×75 mL) then dried over MgSO4 and filtered. The solvent was removed in vacuo and the residue was purified by silica gel chromatography (40 g, 0-100% EtOAc in isohexane) to give methyl 3-chloro-4,5-bis(cyclopentyloxy)benzoate (4) (427 mg, 1.26 mmol, 85% yield): m/z 339 [M+H]+ (ES+); 1H NMR (400 MHz, CDCl3) δ: 7.66 (1H, d), 7.45 (1H, d), 5.05-4.98 (1H, m), 4.87-4.83 (1H, m), 3.89 (3H, s), 1.95-1.55 (16H, m).

Quelle