Sodium Chloride → HCID 22404737, compound

HRID 440667Notes

Reaction equation

HRID 440667 reaction equation
[C:1]([C:3]1[C:11]2[O:10][C:9]([CH3:13])([CH3:12])[CH2:8][C:7]=2[CH:6]=[CH:5][C:4]=1[F:14])#[N:2].[OH-:15].[K+].[Cl-].[Na+]>C(O)(C)(C)C>[CH3:13][C:9]1([CH3:12])[CH2:8][C:7]2[CH:6]=[CH:5][C:4]([F:14])=[C:3]([C:1]([NH2:2])=[O:15])[C:11]=2[O:10]1

Participants

5

Reactant 3

HCID 5234Sodium ChlorideHCID 14797Potassium HydroxideHCID 22404765HCID 22404765, compound

Product 1

HCID 22404737HCID 22404737, compoundYield 88.9%

Reagents, catalysts & solvents 1

HCID 6386tert-ButanolSolvent

Procedure

In a flask were placed 140.0 g (0.732 mole) of 7-cyano-2,3-dihydro-2,2-dimethyl-6-fluorobenzofuran, 147.91 g (2.64 moles) of powdered potassium hydroxide, and 950 mL of t-butanol. This mixture was heated at reflux for 50 minutes after which it was cooled to ambient temperature. It was then poured into a mixture of 1500 mL of crushed ice and 1500 mL of a saturated aqueous solution of sodium chloride. The resulting mixture was extracted twice with 750 mL of ethyl acetate. The extracts were combined and washed once with a saturated aqueous solution of sodium chloride. After being dried over anhydrous magnesium sulfate and filtered, the solvent was evaporated from the filtrate under reduced pressure, yielding 136.09 g of 2,3-dihydro-2,2-dimethyl-6-fluorobenzofuran-7-ylcarboxamide. The NMR spectrum was consistent with the proposed structure.

Workup

  1. customIn a flask were placed
  2. temperatureThis mixture was heated
  3. temperatureat reflux for 50 minutes after which it
  4. extractionThe resulting mixture was extracted twice with 750 mL of ethyl acetate
  5. washwashed once with a saturated aqueous solution of sodium chloride
  6. dry with materialAfter being dried over anhydrous magnesium sulfate
  7. filtrationfiltered
  8. customthe solvent was evaporated from the filtrate under reduced pressure

Sources & evidence

ORD record
ord-a0acb66e78694fd3acea1961a734f35a
Source dataset
uspto-grants-1996_05
Patent number
US05521147

Reaction notes

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