Ethanol → HCID 19029343, compound

HRID 2256281Notes

Reaction equation

HRID 2256281 reaction equation
C(OC(=O)C[C:6]([CH2:8][CH:9]([CH2:18][C:19](=[O:26])CC(OCC)=O)[C:10]1[CH:15]=[CH:14][C:13]([F:16])=[C:12]([F:17])[CH:11]=1)=[O:7])C.[OH-:28].[Na+].C([OH:32])C>>[F:17][C:12]1[CH:11]=[C:10]([CH:9]([CH2:8][C:6]([OH:7])=[O:32])[CH2:18][C:19]([OH:26])=[O:28])[CH:15]=[CH:14][C:13]=1[F:16]

Participants

4

Reactant 3

HCID 702EthanolHCID 14798Sodium HydroxideHCID 131720107HCID 131720107, compound

Product 1

HCID 19029343HCID 19029343, compound

Conditions

Temperature
0 °C

Procedure

Diethyl-3,4-difluorobenzal-bis-acetoacetate (11 g) in ethanol (150 mL) was treated with 50% NaOH (150 mL) and heated at reflux for 4 hours. Approximately 100 mL of solvent was removed by distillation. The remaining solution was cooled to 0° C. and sufficient HCl was added dropwise to adjust the pH to 1. The resulting solution was extracted with EtOAc (3×300 mL) and the combined extracts dried over MgSO4, filtered and concentrated under reduced pressure to give the title compound as a white solid (7.4 g).

Workup

  1. temperatureheated
  2. temperatureat reflux for 4 hours
  3. customApproximately 100 mL of solvent was removed by distillation
  4. additionsufficient HCl was added dropwise
  5. extractionThe resulting solution was extracted with EtOAc (3×300 mL)
  6. dry with materialthe combined extracts dried over MgSO4
  7. filtrationfiltered
  8. concentrationconcentrated under reduced pressure

Sources & evidence

ORD record
ord-5c4ce5b77cc4431b9bcb2fab3e1dbd68
Source dataset
uspto-grants-1997_08
Patent number
US05654316

Reaction notes

Loading…