Hydrochloric Acid → HCID 67867608, compound

HRID 1650815Notes

Reaction equation

HRID 1650815 reaction equation
[CH2:1]([O:13][C:14]1[CH:19]=[CH:18][C:17]([CH2:20][C:21]([N:23]([CH2:25][C:26]([O:28]CC)=O)[CH3:24])=[O:22])=[CH:16][CH:15]=1)[CH2:2][CH2:3][CH2:4][CH2:5][CH2:6][CH2:7][CH2:8][CH2:9][CH2:10][CH2:11][CH3:12].CC(C)([O-])C.[K+].Cl>C1COCC1.CN(C=O)C>[CH3:24][N:23]1[CH2:25][C:26]([OH:28])=[C:20]([C:17]2[CH:18]=[CH:19][C:14]([O:13][CH2:1][CH2:2][CH2:3][CH2:4][CH2:5][CH2:6][CH2:7][CH2:8][CH2:9][CH2:10][CH2:11][CH3:12])=[CH:15][CH:16]=2)[C:21]1=[O:22]

Participants

6

Reactant 3

HCID 313Hydrochloric AcidHCID 14477214HCID 14477214, compoundHCID 23665647Potassium tert-butoxide

Product 1

HCID 67867608HCID 67867608, compoundYield 71%

Reagents, catalysts & solvents 2

HCID 6228DimethylformamideSolventHCID 8028TetrahydrofuranSolvent

Procedure

In a mixture of THF (50 ml) and DMF (10 ml) was dissolved ethyl N-(4-dodecyloxyphenylacetyl)-N-methylaminoacetate (4.0 g, 0.01 mol.). To the solution was added at room temperature potassium tertiary butoxide (1.8 g, 1.6 mol.) and the mixture was stirred for one hour, to which was then added 2N HCl (20 ml), followed by extraction with ethyl acetate. The organic layer was washed with water, dried and concentrated under reduced pressure to give crude crystals. The crude crystals were recrystallized from IPE - ethyl acetate to give N-methyl-3-(4-dodecyloxyphenyl)-4-hydroxy-3-pyrrolin-2-one (4-b, 2.4 g, 71%).

Workup

  1. extractionfollowed by extraction with ethyl acetate
  2. washThe organic layer was washed with water
  3. customdried
  4. concentrationconcentrated under reduced pressure
  5. customto give crude crystals
  6. customThe crude crystals were recrystallized from IPE - ethyl acetate

Sources & evidence

ORD record
ord-e9713c09243d4bde8a8368871ee3e0e7
Source dataset
uspto-grants-1990_05
Patent number
US04925868

Reaction notes

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