Hydrochloric Acid → (Z)-3-(7-cyclopentyloxy-4-methyloxycarbonylbenzo[b]furan-2-yl)-2-propenoic acid

HRID 1091865Notes

Reaction equation

HRID 1091865 reaction equation
[CH3:1][O:2][C:3]([C:5]1[C:13]2[CH:12]=[C:11](C=O)[O:10][C:9]=2[C:8]([O:16][CH:17]2[CH2:21][CH2:20][CH2:19][CH2:18]2)=[CH:7][CH:6]=1)=[O:4].[C:22](O)(=O)[CH2:23][C:24]([OH:26])=[O:25].N1CCCCC1.Cl>C1(C)C=CC=CC=1>[CH:17]1([O:16][C:8]2[C:9]3[O:10][C:11](/[CH:22]=[CH:23]\[C:24]([OH:26])=[O:25])=[CH:12][C:13]=3[C:5]([C:3]([O:2][CH3:1])=[O:4])=[CH:6][CH:7]=2)[CH2:18][CH2:19][CH2:20][CH2:21]1

Participants

6

Reactant 4

HCID 313Hydrochloric AcidHCID 867Malonic AcidHCID 8082PiperidineHCID 24988271Methyl-2-formyl-7-cyclopentyloxybenzo[b]furan-4-carboxylate

Product 1

HCID 66592835(Z)-3-(7-cyclopentyloxy-4-methyloxycarbonylbenzo[b]furan-2-yl)-2-propenoic acidYield 66.3%

Reagents, catalysts & solvents 1

HCID 1140TolueneSolvent

Procedure

To a well stirred solution of Methyl-2-formyl-7-cyclopentyloxybenzo[b]furan-4-carboxylate (21.0 g, 0.0868 moles) in toluene (250.0 mL) was added malonic acid (13.5 g, 0.1302 moles) and Piperidine (5.0 ml). The reaction mixture was then refluxed for 3-4 hours. Reaction mixture was cooled to room temperature, acidified with 10% aqueous HCl solution and extracted with ethyl acetate (2×250 mL). The combined organic layers were washed with water (2×100 mL) and dried over anhydrous sodium sulfate. Removal of solvent under vacuo gave product (19 g) as light yellow solid.

Workup

  1. temperatureThe reaction mixture was then refluxed for 3-4 hours
  2. customReaction mixture
  3. extractionextracted with ethyl acetate (2×250 mL)
  4. washThe combined organic layers were washed with water (2×100 mL)
  5. dry with materialdried over anhydrous sodium sulfate
  6. customRemoval of solvent under vacuo

Sources & evidence

ORD record
ord-bfc3571c365541bfad43879d8cf1cbe9
Source dataset
uspto-grants-2012_03
Patent number
US08129401B2

Reaction notes

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