Water → HCID 18348736, compound

HRID 2268030Notes

Reaction equation

HRID 2268030 reaction equation
C([N-]C(C)C)(C)C.[Li+].[CH:9]1([CH2:12][C:13]([OH:15])=[O:14])[CH2:11][CH2:10]1.[F:16][C:17]1[CH:18]=[C:19]([CH:22]=[CH:23][C:24]=1[F:25])[CH:20]=[O:21].O>C1COCC1>[CH:9]1([CH:12]([CH:20]([C:19]2[CH:22]=[CH:23][C:24]([F:25])=[C:17]([F:16])[CH:18]=2)[OH:21])[C:13]([OH:15])=[O:14])[CH2:11][CH2:10]1

Participants

6

Reactant 4

HCID 962WaterHCID 138440Cyclopropaneacetic acidHCID 5880883,4-DifluorobenzaldehydeHCID 2724682Lithium diisopropylamide

Product 1

HCID 18348736HCID 18348736, compound

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent2×

Procedure

To a stirred solution of lithium diisopropylamide (2.0M in hexanes, 46.4 mL, 92.8 mmol) in 20 mL of THF at −40° C. under a nitrogen atmosphere was added cyclopropylacetic acid (4.65g in 20 mL of THF, 46.4 mmol), dropwise. The mixture was stirred in the cold for 15 minutes and warmed to ambient temperature. After 1 hour, the reaction slurry was cooled in an ice bath and 3,4-difluorobenzaldehyde (5.2 mL, 47.1 mmol) in 10 mL of THF was added dropwise. The mixture was warmed to ambient temperature and allowed to stir for 2 hours. The mixture was poured into 200 mL of cold water and the layers separated. The organic layer was washed with water (3X), and the combined aqueous layers were washed with ethyl ether (2X), and then acidified with 3N hydrochloric acid. The water layer was extracted with ethyl ether (3X) and the combined ether layers were dried over sodium sulfate, filtered, and evaporated to dryness to yield the title compound as an oil.

Workup

  1. waitAfter 1 hour
  2. temperaturethe reaction slurry was cooled in an ice bath
  3. temperatureThe mixture was warmed to ambient temperature
  4. stirringto stir for 2 hours
  5. customthe layers separated
  6. washThe organic layer was washed with water (3X)
  7. washthe combined aqueous layers were washed with ethyl ether (2X)
  8. extractionThe water layer was extracted with ethyl ether (3X)
  9. dry with materialthe combined ether layers were dried over sodium sulfate
  10. filtrationfiltered
  11. customevaporated to dryness

Sources & evidence

ORD record
ord-ea3a9dc197864af8b839abaf1400aafa
Source dataset
uspto-grants-2001_12
Patent number
US06326372B1

Reaction notes

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