반응 #91008

반응 방정식

methyl 3-chloro-4,5-dihydroxybenzoate

Methyl 3-chloro-4,5-dihydroxybenzoate

iodocyclopentane

potassium carbonate

→

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

수율 85.1%

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

수율 85.1%

용매

DMF

반응 조건

후처리

1. 1
   온도The reaction mixture was cooled to room temperature
2. 2
   기타partitioned between 1M HCl (75 mL) and EtOAc (100 mL)
3. 3
   기타The phases were separated
4. 4
   세척the organic phase was washed with brine (2×75 mL)
5. 5
   건조then dried over MgSO4
6. 6
   여과filtered
7. 7
   기타The solvent was removed in vacuo
8. 8
   기타the residue was purified by silica gel chromatography (40 g, 0-100% EtOAc in isohexane)

실험 절차

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).

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