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

HRID 62730

반응식

HRID 62730 반응식
[Cl:1][C:2]1[CH:3]=[C:4]([CH:9]=[C:10]([OH:13])[C:11]=1[OH:12])[C:5]([O:7][CH3:8])=[O:6].I[CH:15]1[CH2:19][CH2:18][CH2:17][CH2:16]1.C(=O)([O-])[O-].[K+].[K+]>CN(C=O)C>[Cl:1][C:2]1[CH:3]=[C:4]([CH:9]=[C:10]([O:13][CH:15]2[CH2:19][CH2:18][CH2:17][CH2:16]2)[C:11]=1[O:12][CH:15]1[CH2:19][CH2:18][CH2:17][CH2:16]1)[C:5]([O:7][CH3:8])=[O:6]

참가 물질

5

반응물 3

HCID 11430Potassium CarbonateHCID 73784IodocyclopentaneHCID 21649010Methyl 3-chloro-4,5-dihydroxybenzoate

생성물 1

HCID 67041558Methyl 3-chloro-4,5-bis(cyclopentyloxy)benzoate수율 85.1%

시약·촉매·용매 1

HCID 6228Dimethylformamide용매

반응 조건

온도
70 °C

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).

후처리

  1. temperatureThe reaction mixture was cooled to room temperature
  2. custompartitioned between 1M HCl (75 mL) and EtOAc (100 mL)
  3. customThe phases were separated
  4. washthe organic phase was washed with brine (2×75 mL)
  5. dry with materialthen dried over MgSO4
  6. filtrationfiltered
  7. customThe solvent was removed in vacuo
  8. customthe residue was purified by silica gel chromatography (40 g, 0-100% EtOAc in isohexane)

출처 및 근거

ORD 기록
ord-ae67a304fc094f0b89a528e50d0ef65d
출처 데이터셋
uspto-grants-2016_09
특허 번호
US09447028B2

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