Hydrochloric Acid → HCID 53932036, compound

HRID 1109367Notes

Reaction equation

HRID 1109367 reaction equation
C([N:4]1[CH2:8][CH2:7][C:6](=[CH:9][C:10]2[CH:15]=[C:14]([CH:16]([CH3:18])[CH3:17])[C:13]([OH:19])=[C:12]([CH:20]([CH3:22])[CH3:21])[CH:11]=2)[C:5]1=[O:23])(=O)C.[OH-].[Na+].Cl>CO.C1COCC1>[CH:16]([C:14]1[CH:15]=[C:10]([CH:11]=[C:12]([CH:20]([CH3:22])[CH3:21])[C:13]=1[OH:19])[CH:9]=[C:6]1[CH2:7][CH2:8][NH:4][C:5]1=[O:23])([CH3:18])[CH3:17]

Participants

6

Reactant 3

HCID 313Hydrochloric AcidHCID 14798Sodium HydroxideHCID 53762281HCID 53762281, compound

Product 1

HCID 53932036HCID 53932036, compoundYield 100%

Reagents, catalysts & solvents 2

HCID 887MethanolSolventHCID 8028TetrahydrofuranSolvent

Procedure

To a solution of 810 mg (2.57 mmol) of the thus obtained 1-acetyl-3-(3,5-di-isopropyl-4-hydroxybenzylidene)pyrrolidin-2-one in 5 ml of methanol and 10 ml of THF was added 2 ml of 1N aq. sodium hydroxide at room temperature and the mixture was stirred for 3 hours. the reaction mixture was poured into ice-water containing ethyl acecate and 3 ml of 1N hydrochloric acid. The ethyl acetate layer was washed with water and saturated brine, dried over magnesium sulfate and evaporated under reduced pressure to give a residue, which was crystallized from a ether/n-hexane mixture to give 800 mg of the objective compound as yellowish white crystal in 100% yield.

Workup

  1. washThe ethyl acetate layer was washed with water and saturated brine
  2. dry with materialdried over magnesium sulfate
  3. customevaporated under reduced pressure
  4. customto give a residue, which
  5. customwas crystallized from a ether/n-hexane mixture

Sources & evidence

ORD record
ord-ddd90223e1eb48f2a577b9db00db1680
Source dataset
uspto-grants-1994_06
Patent number
US05319099

Reaction notes

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