Hydrochloric Acid → 1-Carbamoyl-3-(3-ethoxy-4-hydroxybenzylidene)pyrrolidin-2-one
Reaction equation
[Br-].[C:2]([N:5]1[CH2:9][CH2:8][CH:7]([P+](C2C=CC=CC=2)(C2C=CC=CC=2)C2C=CC=CC=2)[C:6]1=[O:29])(=[O:4])[NH2:3].[CH2:30]([O:32][C:33]1[CH:34]=[C:35]([CH:38]=[CH:39][C:40]=1[OH:41])[CH:36]=O)[CH3:31].C(N(CC)CC)C.[OH-].[Na+].Cl>C(O)C.C(OC(C)C)(C)C.C(OCC)(=O)C>[C:2]([N:5]1[CH2:9][CH2:8][C:7](=[CH:36][C:35]2[CH:38]=[CH:39][C:40]([OH:41])=[C:33]([O:32][CH2:30][CH3:31])[CH:34]=2)[C:6]1=[O:29])(=[O:4])[NH2:3]Participants
Reactant 5
Product 1
Reagents, catalysts & solvents 3
Conditions
- Temperature
- 60 °C
Procedure
To a solution of 939 mg (2 mmol) of (1-carbamoyl-2-oxopyrrolidin-3-yl)triphenylphosphonium bromide in ethanol (16 ml) were added 332 mg (2 mmol) of 3-ethoxy-4-hydroxybenzaldehyde and 558 μl (4 mmol) of triethylamine, and the mixture was stirred at 60° C. for 2 hours. The reaction mixture was evaporated to give a residue, which was dissolved in diisopropyl ether and treated with 4 ml of 1N aq. sodium hydroxide. The aqueous layer was made acid with 1N hydrochloric acid under ice-cooling and the product was dissolved in ethyl acetate, washed with water and saturated brine, dried over magnesium sulfate and evaporated to give a residue, which was crystallized from a dichloromethane/n-hexane mixture to give 143 mg of the objective compound (Ia-19) in 26% yield.
Workup
- customThe reaction mixture was evaporated
- customto give a residue, which
- temperaturecooling
- washwashed with water and saturated brine
- dry with materialdried over magnesium sulfate
- customevaporated
- customto give a residue, which
- customwas crystallized from a dichloromethane/n-hexane mixture
Sources & evidence
- ORD record
- ord-aae0609a87284ce48aae3f17fb7e3fb1
- Source dataset
- uspto-grants-1994_06
- Patent number
- US05319099
Reaction notes
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