Sodium Chloride → 2-Methyl-2-phenyl-5-[2-(2-pyridinyl)ethenyl]-3(2H)-furanone

HRID 359381

Reaction equation

[N:1]1[CH:6]=[CH:5][CH:4]=[CH:3][C:2]=1[CH:7]=O.[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.CCCCCCC=CCCC.[Cl-].[Na+]>C(O)C>[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]([CH:16]=[CH:7][C:2]2[CH:3]=[CH:4][CH:5]=[CH:6][N:1]=2)[O:11]1

Participants

Conditions

Temperature: 80 °C

Procedure

To a solution of 2-pyridinecarboxaldehyde (1.2 mL, 1.2 mM) and 2,5-dimethyl-2-phenyl-3(2H)-furanone (1.5 g, 8 mM) in ethanol (15 mL), was added 1,8-diazebicyclo[4.5.0]undec-7ene (DBU, 0.2 mL, 1.3 mM). The reaction solution was heated at 80° C. for 5 hours. After the reaction solution cooled to room temperature, saturated aqueous sodium chloride (400 mL) was added. The aqueous layer was extracted with dichloromethane (3×100 mL). The combined dichloromethane extracts were washed with saturated aqueous sodium chloride (50 mL), dried over MgSO4, filtered and concentrated to give a yellow solid. Purification by trituration with 10% diethyl ether in hexane gave a pale pink solid (887 mg, 40% yield), m.p. 74.5°-76° C.

Workup

temperatureAfter the reaction solution cooled to room temperature
extractionThe aqueous layer was extracted with dichloromethane (3×100 mL)
washThe combined dichloromethane extracts were washed with saturated aqueous sodium chloride (50 mL)
dry with materialdried over MgSO4
filtrationfiltered
concentrationconcentrated
customto give a yellow solid
customPurification by trituration with 10% diethyl ether in hexane

Sources & evidence

ORD record: ord-06b83c91a9b2484ea66f8a07b806b0af
Source dataset: uspto-grants-1991_03
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US05001126

Linked notes

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