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

HRID 62730

Reaction equation

[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]

Participants

Conditions

Temperature: 70 °C

Procedure

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).

Workup

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

Sources & evidence

ORD record: ord-ae67a304fc094f0b89a528e50d0ef65d
Source dataset: uspto-grants-2016_09
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US09447028B2

Linked notes

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