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

HRID 1767191Notes

Reaction equation

HRID 1767191 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.C1C=CC([P]([Pd]([P](C2C=CC=CC=2)(C2C=CC=CC=2)C2C=CC=CC=2)([P](C2C=CC=CC=2)(C2C=CC=CC=2)C2C=CC=CC=2)[P](C2C=CC=CC=2)(C2C=CC=CC=2)C2C=CC=CC=2)(C2C=CC=CC=2)C2C=CC=CC=2)=CC=1>[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

6

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 esterYield 39.3%

Reagents, catalysts & solvents 2

HCID 178418397HCID 178418397, compoundCatalystHCID 80711,2-DimethoxyethaneSolvent

Procedure

3-(2-Bromocyclopent-1-enyl)-benzoic acid ethyl ester (148 mg, 0.5 mmol), tetrakis(triphenylphosphine)palladium (0) (30 mg), potassium carbonate (0.20 g) and (2-benzyloxy-5-chlorophenyl) boronic acid (150 mg, 0.5 mmol) in dimethoxyethane (5 mL) were refluxed for 17 h under nitrogen. The reaction mixture was then filtered through Kieselguhr and evaporated down to an oil. Purification was carried out on a Water's separation pack (10 g) with dichloromethane/iso-hexane to give the product (85 mg).

Workup

  1. filtrationThe reaction mixture was then filtered through Kieselguhr
  2. customevaporated down to an oil
  3. customPurification
  4. customseparation pack (10 g) with dichloromethane/iso-hexane

Sources & evidence

ORD record
ord-f6432b3331064d04b6791f58e64bc0ee
Source dataset
uspto-grants-2007_06
Patent number
US07232821B2

Reaction notes

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