Potassium Carbonate → 3-[2-(2-Methoxy-phenyl)-cyclopent-1-enyl]-benzoic Acid Ethyl Ester

HRID 1767203Notes

Reaction equation

HRID 1767203 reaction equation
[CH3:1][O:2][C:3]1[CH:8]=[CH:7][CH:6]=[CH:5][C:4]=1B(O)O.[CH2:12]([O:14][C:15](=[O:28])[C:16]1[CH:21]=[CH:20][CH:19]=[C:18]([C:22]2[CH2:26][CH2:25][CH2:24][C:23]=2Br)[CH:17]=1)[CH3:13].C(=O)([O-])[O-].[K+].[K+].C1(C)C=CC=CC=1.C(O)C>C(OCC)C.O.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>[CH2:12]([O:14][C:15](=[O:28])[C:16]1[CH:21]=[CH:20][CH:19]=[C:18]([C:22]2[CH2:26][CH2:25][CH2:24][C:23]=2[C:4]2[CH:5]=[CH:6][CH:7]=[CH:8][C:3]=2[O:2][CH3:1])[CH:17]=1)[CH3:13]

Participants

7

Reactant 4

HCID 11430Potassium CarbonateHCID 27339582-Methoxyphenylboronic acidHCID 21863594Toluene ethanolHCID 578620843-(2-Bromo-cyclopent-1-enyl)benzoic Acid Ethyl Ester

Product 1

HCID 695079153-[2-(2-Methoxy-phenyl)-cyclopent-1-enyl]-benzoic Acid Ethyl Ester

Reagents, catalysts & solvents 2

HCID 178418397HCID 178418397, compoundCatalystHCID 21584184Diethylether waterSolvent

Procedure

A mixture of 2-methoxyphenylboronic acid (510 mg, 3.36 mmol), 3-(2-bromo-cyclopent-1-enyl)-benzoic acid ethyl ester (840 mg, 2.85 mmol), potassium carbonate (3.18 g, 23.04 mmol) and tetrakis(triphenylphosphine)palladium(0) (370 mg, 0.32 mmol) was stirred and heated in 1:1 toluene/ethanol (30 ml) at 90° C. under nitrogen for 4 hours. After cooling the mixture was diluted with diethyl ether/water and the organic phase dried (MgSO4), evaporated to dryness and the residue purified on Biotage using ethyl acetate/iso-hexane (1:19) to yield the title compound as a colourless gum. (615 mg, 67%).

Workup

  1. temperatureAfter cooling the mixture
  2. dry with materialthe organic phase dried (MgSO4)
  3. customevaporated to dryness
  4. customthe residue purified on Biotage

Sources & evidence

ORD record
ord-9d1e9ddc8db341c0b108dbfaf921c354
Source dataset
uspto-grants-2007_06
Patent number
US07232821B2

Reaction notes

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