Malonic Acid → 3-(1-Benzothiophen-3-yl)prop-2-enoic acid

HRID 1353583Notes

Reaction equation

HRID 1353583 reaction equation
[S:1]1[C:5]2[CH:6]=[CH:7][CH:8]=[CH:9][C:4]=2[C:3]([CH:10]=O)=[CH:2]1.C(O)(=O)[CH2:13][C:14]([OH:16])=[O:15].N1CCCCC1>N1C=CC=CC=1>[S:1]1[CH:2]=[C:3]([CH:10]=[CH:13][C:14]([OH:16])=[O:15])[C:4]2[CH:9]=[CH:8][CH:7]=[CH:6][C:5]1=2

Participants

5

Reactant 3

HCID 867Malonic AcidHCID 8082PiperidineHCID 2273281-Benzothiophene-3-carbaldehyde

Product 1

HCID 534270043-(1-Benzothiophen-3-yl)prop-2-enoic acid

Reagents, catalysts & solvents 1

HCID 1049PyridineSolvent

Conditions

Temperature
110 °C

Procedure

A suspension of 1-benzothiophene-3-carbaldehyde (4.9 g, 0.03 mol), malonic acid (6.6 g, 0.06 mol) and piperidine (1 mL) in 100 mL anhydrous pyridine was heated at 110° C. overnight. The reaction mixture was cooled to room temperature and the solvent was removed in vacuo. The residue was taken up in 100 mL of water and 1 N hydrochloric acid was added to adjust the pH of this solution to ca. 3. The suspension was filtered and the yellow solid was collected, washed with water (3×50 mL) and concentrated in vacuo to give the indicated product with 95% purity (5.65 g, 91%).

Workup

  1. temperatureThe reaction mixture was cooled to room temperature
  2. customthe solvent was removed in vacuo
  3. addition1 N hydrochloric acid was added
  4. filtrationThe suspension was filtered
  5. customthe yellow solid was collected
  6. washwashed with water (3×50 mL)
  7. concentrationconcentrated in vacuo
  8. customto give the indicated product with 95% purity (5.65 g, 91%)

Sources & evidence

ORD record
ord-916cfcbb2b5f4653a086e29894eadb65
Source dataset
uspto-grants-2007_05
Patent number
US07220862B2

Reaction notes

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