Participants
| Role | Name | HCID | Charge |
|---|
| Reactant | Sodium Chloride | HCID 5234 | — |
| Reactant | 1-Methyl-1H-pyrrole-2-carbaldehyde | HCID 14504 | — |
| Reactant | Sodium Hydroxide | HCID 14798 | — |
| Reactant | 3(2H)-Furanone, 2,2,5-trimethyl- | HCID 137080 | — |
| Solvent | Ethanol | HCID 702 | — |
| Product | HCID 54417238 | HCID 54417238 | 65% |
Reaction Steps
To a solution of 1methyl-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.
Provenance & Evidence
| DOI | 10.6084/m9.figshare.5104873.v1 |
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| Patent number | US05017601 |
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| Source dataset | uspto-grants-1991_05 |
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| ORD ID | ord-8529cdd237564e2ca84ff3f3d566e24d |
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| Source note | uspto-grants-1991_05 |
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