Potassium Carbonate → 3-[2-(2-Benzyloxy-5-chlorophenyl)cyclopent-1-enyl] benzoic acid ethyl ester

HRID 1767187Notes

Reaction equation

HRID 1767187 reaction equation
[CH2:1]([O:3][C:4](=[O:17])[C:5]1[CH:10]=[CH:9][CH:8]=[C:7]([C:11]2[CH2:15][CH2:14][CH2:13][C:12]=2Br)[CH:6]=1)[CH3:2].C(=O)([O-])[O-].[K+].[K+].[CH2:24]([O:31][C:32]1[CH:37]=[CH:36][C:35]([Cl:38])=[CH:34][C:33]=1B(O)O)[C:25]1[CH:30]=[CH:29][CH:28]=[CH:27][CH:26]=1>C(COC)OC>[CH2:1]([O:3][C:4](=[O:17])[C:5]1[CH:10]=[CH:9][CH:8]=[C:7]([C:11]2[CH2:15][CH2:14][CH2:13][C:12]=2[C:33]2[CH:34]=[C:35]([Cl:38])[CH:36]=[CH:37][C:32]=2[O:31][CH2:24][C:25]2[CH:26]=[CH:27][CH:28]=[CH:29][CH:30]=2)[CH:6]=1)[CH3:2]

Participants

5

Reactant 3

HCID 11430Potassium CarbonateHCID 41987402-Benzyloxy-5-chlorobenzeneboronic acidHCID 57862084HCID 57862084, compound

Product 1

HCID 695075793-[2-(2-Benzyloxy-5-chlorophenyl)cyclopent-1-enyl] benzoic acid ethyl ester

Reagents, catalysts & solvents 1

HCID 80711,2-DimethoxyethaneSolvent

Procedure

3-(2-Bromocyclopent-1-enyl)-benzoic acid ethyl ester (0.148 g, 0.0005 mol), Pd(0)[PPh3]4 (30 mg), potassium carbonate (0.2 g) and (2-benzyloxy-5-chlorophenyl) boronic acid (150 mg, 0.0005 mol) in dimethoxyethane (5 mL) were refluxed for 17 h under nitrogen. The reaction mixture was then filtered through Kieselghur and evaporated down to an oil. Purification was carried out on a Water's separation pack (10 g) with dichloromethane/isohexane giving the product (85 mg).

Workup

  1. filtrationThe reaction mixture was then filtered through Kieselghur
  2. customevaporated down to an oil
  3. customPurification
  4. customseparation pack (10 g) with dichloromethane/isohexane giving the product (85 mg)

Sources & evidence

ORD record
ord-219d63d4c00648e1a103c6941cdb8712
Source dataset
uspto-grants-2007_06
Patent number
US07232821B2

Reaction notes

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