Sodium Chloride → HCID 54417238, compound
Reaction equation
[CH3:1][N:2]1[CH:6]=[CH:5][CH:4]=[C:3]1[CH:7]=O.[CH3:9][C:10]1([CH3:17])[C:14](=[O:15])[CH:13]=[C:12]([CH3:16])[O:11]1.[OH-].[Na+].[Cl-].[Na+]>C(O)C>[CH3:9][C:10]1([CH3:17])[C:14](=[O:15])[CH:13]=[C:12]([CH:16]=[CH:7][C:3]2[N:2]([CH3:1])[CH:6]=[CH:5][CH:4]=2)[O:11]1Participants
6
Reactant 4
Product 1
Reagents, catalysts & solvents 1
Conditions
- Temperature
- 70 °C
Procedure
To a solution of 1-methyl-2-pyrrolecarboxaldehyde (1.4 g, 12.7 mM) and 2,2,5-trimethyl-3(2H)-furanone (2.0 g, 15.9 mM) in ethanol (100 mL), was added 1N aqueous sodium hydroxide (1.6 mL, 1.6 mM). The reaction solution was heated at 70° C. for 48 hours. After the reaction solution was cooled to 0° C., saturated aqueous sodium chloride (400 mL) was added. The aqueous layer was extracted with ethyl acetate (3×100 mL). The combined ethyl acetate extracts were washed with saturated aqueous sodium chloride (50 mL), dried over MgSO4, filtered and concentrated to give a brown solid. The crude product was purified by chromatography (silica gel, pet. ether-ethyl acetate) to give orange crystals (1.8 g, 65% yield), m.p. 98.5°-100° C.
Workup
- temperatureAfter the reaction solution was cooled to 0° C.
- extractionThe aqueous layer was extracted with ethyl acetate (3×100 mL)
- washThe combined ethyl acetate extracts were washed with saturated aqueous sodium chloride (50 mL)
- dry with materialdried over MgSO4
- filtrationfiltered
- concentrationconcentrated
- customto give a brown solid
- customThe crude product was purified by chromatography (silica gel, pet. ether-ethyl acetate)
Sources & evidence
- ORD record
- ord-4baa5459d5c340c692bd2218272d71e3
- Source dataset
- uspto-grants-1991_03
- Patent number
- US05001126
Reaction notes
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