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

HRID 62730

反応式

HRID 62730 の反応式
[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]

参加物

5

反応物 3

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

生成物 1

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

試薬・触媒・溶媒 1

HCID 6228Dimethylformamide溶媒

反応条件

温度
70 °C

実験手順

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).

後処理

  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)

出典と根拠

ORDレコード
ord-ae67a304fc094f0b89a528e50d0ef65d
出典データセット
uspto-grants-2016_09
特許番号
US09447028B2

関連ノート

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