Pyruvic Acid → HCID 131735958, compound

HRID 2207926Notes

Reaction equation

HRID 2207926 reaction equation
[C:1]([OH:6])(=[O:5])[C:2]([CH3:4])=[O:3].[OH-].[Na+].[Br:9][C:10]1[CH:17]=[CH:16][C:13]([CH:14]=O)=[C:12]([F:18])[CH:11]=1>C(O)C>[Br:9][C:10]1[CH:17]=[CH:16][C:13]([CH:14]=[CH:4][C:2](=[O:3])[C:1]([OH:6])=[O:5])=[C:12]([F:18])[CH:11]=1

Participants

5

Procedure

A solution of pyruvic acid (1.9 mL, 27.1 mmol) in ethanol (2.5 mL) was added to a 0.5 M sodium hydroxide solution (74.0 mL). The reaction mixture was stirred at room temperature for 10 minutes and then a solution of 4-bromo-2-fluorobenzaldehyde (5.0 g, 24.6 mmol) in ethanol (22.5 mL) was slowly added thereto at room temperature for 1 hour. The reaction mixture was stirred at room temperature for 18 hours and then filtered. The resulting solid was washed with ethyl acetate, diluted with a 1N hydrochloric acid solution and then extracted with ethyl acetate. The extract was washed with distilled water and brine, dried on anhydrous magnesium sulfate, and then concentrated under reduced pressure to give 5.5 g of the titled compound as a yellow solid.

Workup

  1. waitat room temperature for 1 hour
  2. stirringThe reaction mixture was stirred at room temperature for 18 hours
  3. filtrationfiltered
  4. washThe resulting solid was washed with ethyl acetate
  5. additiondiluted with a 1N hydrochloric acid solution
  6. extractionextracted with ethyl acetate
  7. washThe extract was washed with distilled water and brine
  8. dry with materialdried on anhydrous magnesium sulfate
  9. concentrationconcentrated under reduced pressure

Sources & evidence

ORD record
ord-b3c07a02bfe647d99d36737ba0e6e0dc
Source dataset
uspto-grants-2016_06
Patent number
US09376420B2

Reaction notes

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