Malonic Acid → HCID 58043931, compound

HRID 1919127Notes

Reaction equation

HRID 1919127 reaction equation
[S:1]1[CH:5]=[C:4]([CH:6]=O)[C:3]2[CH:8]=[CH:9][CH:10]=[CH:11][C:2]1=2.C(O)(=O)[CH2:13][C:14]([OH:16])=[O:15].N1CCCCC1>N1C=CC=CC=1>[S:1]1[C:2]2[CH:11]=[CH:10][CH:9]=[CH:8][C:3]=2[C:4](/[CH:6]=[CH:13]\[C:14]([OH:16])=[O:15])=[CH:5]1

Participants

5

Reactant 3

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

Product 1

HCID 58043931HCID 58043931, compoundYield 89%

Reagents, catalysts & solvents 1

HCID 1049PyridineSolvent

Conditions

Temperature
110 °C

Procedure

A suspension of benzo[b]thiophene-3-carbaldehyde (4.9 g, 30 mol), malonic acid (6.6 g, 60 mmol) and piperidine (1 mL) in 100 mL anhydrous pyridine was heated at 110° C. for 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 resulting suspension was filtered and the yellow solid was collected, washed with water (3×30 mL) dried in vacuo to give 329a as a yellow solid (5.5 g, 89%). MS: [M+H]+ 205.

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 resulting suspension was filtered
  5. customthe yellow solid was collected
  6. washwashed with water (3×30 mL)
  7. customdried in vacuo

Sources & evidence

ORD record
ord-c392e72248b3486b82577a57a79194a8
Source dataset
uspto-grants-2013_12
Patent number
US08618107B2

Reaction notes

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