Sodium Chloride → 2-Phenyl-2-methyl-5-[2-(3-pyridinyl)ethenyl]-3(2H)-furanone

HRID 359379

Reaction equation

[N:1]1[CH:6]=[CH:5][CH:4]=[C:3]([CH:7]=O)[CH:2]=1.[CH3:9][C:10]1([C:17]2[CH:22]=[CH:21][CH:20]=[CH:19][CH:18]=2)[C:14](=[O:15])[CH:13]=[C:12]([CH3:16])[O:11]1.[OH-].[Na+].[Cl-].[Na+]>C(O)C>[C:17]1([C:10]2([CH3:9])[C:14](=[O:15])[CH:13]=[C:12]([CH:16]=[CH:7][C:3]3[CH:2]=[N:1][CH:6]=[CH:5][CH:4]=3)[O:11]2)[CH:18]=[CH:19][CH:20]=[CH:21][CH:22]=1

Participants

Conditions

Temperature: 60 °C

Procedure

To a solution of 3-pyridinecarboxaldehyde (1.03 g, 9.6 mM) and 2,5-dimethyl-2-phenyl-3(2H)-furanone (1.0 g, 8 mM) in ethanol (50 mL), was added 1N aqueous sodium hydroxide (2.4 mL, 2.4 mM). The reaction solution was heated at 60° C. for 8 hours. After the reaction solution cooled to room temperature, saturated aqueous sodium chloride (200 mL) was added. The aqueous layer was extracted with diethyl ether (3×100 mL). The combined ethereal 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 afford a yellow crystalline solid (0.8 g, 36.3% yield), m.p. 106°-108° C.

Workup

temperatureAfter the reaction solution cooled to room temperature
extractionThe aqueous layer was extracted with diethyl ether (3×100 mL)
washThe combined ethereal 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-930e8ec0b61c4a61a94ed7dd05e90d65
Source dataset: uspto-grants-1991_03
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US05001126

Linked notes

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