Methyl Ethyl Ketone → 5-{2-[5-Chloro-2-(4-chlorobenzyloxy)-phenyl]-cyclopent-1-enyl}-nicotinic Acid Ethyl Ester

HRID 1767196Notes

Reaction equation

HRID 1767196 reaction equation
[CH2:1]([O:3][C:4](=[O:24])[C:5]1[CH:10]=[C:9]([C:11]2[CH2:15][CH2:14][CH2:13][C:12]=2[C:16]2[CH:21]=[C:20]([Cl:22])[CH:19]=[CH:18][C:17]=2[OH:23])[CH:8]=[N:7][CH:6]=1)[CH3:2].[Cl:25][CH:26](Br)[C:27]1C=CC=C[CH:28]=1.C(=O)([O-])[O-].[K+].[K+].[CH3:40][C:41](=O)[CH2:42][CH3:43]>>[CH2:1]([O:3][C:4](=[O:24])[C:5]1[CH:10]=[C:9]([C:11]2[CH2:15][CH2:14][CH2:13][C:12]=2[C:16]2[CH:21]=[C:20]([Cl:22])[CH:19]=[CH:18][C:17]=2[O:23][CH2:40][C:41]2[CH:28]=[CH:27][C:26]([Cl:25])=[CH:43][CH:42]=2)[CH:8]=[N:7][CH:6]=1)[CH3:2]

Participants

5

Reactant 4

HCID 6569Methyl Ethyl KetoneHCID 11430Potassium CarbonateHCID 11805852Chlorobenzyl bromideHCID 695077915-{2-[5-Chloro-2-(hydroxy)-phenyl]cyclopent-1-enyl}-nicotinic Acid Ethyl Ester

Product 1

HCID 588876485-{2-[5-Chloro-2-(4-chlorobenzyloxy)-phenyl]-cyclopent-1-enyl}-nicotinic Acid Ethyl Ester

Procedure

5-{2-[5-Chloro-2-(hydroxy)-phenyl]-cyclopent-1-enyl}-nicotinic acid ethyl ester (138 mg, 0.43 mmol) was treated with 4 chlorobenzyl bromide (0.130 g, 60 mmol) and potassium carbonate (1.000 g) and 2-butanone (5 mL) at reflux for 18 hrs. Upon cooling, the mixture was filtered through highflo and reduced down to an oil. The product was purified using a Water's sep-pak cartridge (10 g) to give (90 mg, 44%).

Workup

  1. temperatureat reflux for 18 hrs
  2. temperatureUpon cooling
  3. filtrationthe mixture was filtered through highflo
  4. customThe product was purified
  5. customto give (90 mg, 44%)

Sources & evidence

ORD record
ord-a5572b54891645c09e3515445465f171
Source dataset
uspto-grants-2007_06
Patent number
US07232821B2

Reaction notes

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