Sodium Hydroxide → 2,2-Dimethyl-5-[2-(4-fluorophenyl)ethenyl]-3(2H)-furanone

HRID 359357

Reaction equation

[CH3:1][C:2]1([CH3:9])[C:6](=[O:7])[CH:5]=[C:4]([CH3:8])[O:3]1.[F:10][C:11]1[CH:18]=[CH:17][C:14]([CH:15]=O)=[CH:13][CH:12]=1.[OH-].[Na+]>C(O)C.[Cl-].[Na+].O>[CH3:1][C:2]1([CH3:9])[C:6](=[O:7])[CH:5]=[C:4]([CH:8]=[CH:15][C:14]2[CH:17]=[CH:18][C:11]([F:10])=[CH:12][CH:13]=2)[O:3]1

Participants

Conditions

Temperature: 50 °C

Procedure

To a solution of 2,2,5-trimethyl-3(2H)-furanone (2.0 g, 15.9 mM) and 4-fluorobenzaldehyde (1.6 g, 13.2 mM) in ethanol (100 mL), was added 1N aqueous sodium hydroxide (1.6 mL, 1.6 mM). The reaction solution was heated at 50° C. for four hours. After the reaction solution was cooled to room temperature and diluted with saturated aqueous sodium chloride (200 mL) and water (200 mL), the aqueous solution was extracted with diethyl ether (2×100 mL). The combined ethereal extracts were washed with saturated aqueous sodium chloride (25 mL), dried over magnesium sulfate, filtered and concentrated at reduced pressure to afford a dark yellow crystalline solid. The crude product was recrystallized from hexane to give light yellow crystals (1.8 g, 45% yield), m.p. 55°-57° C.

Workup

temperatureAfter the reaction solution was cooled to room temperature
extractionthe aqueous solution was extracted with diethyl ether (2×100 mL)
washThe combined ethereal extracts were washed with saturated aqueous sodium chloride (25 mL)
dry with materialdried over magnesium sulfate
filtrationfiltered
concentrationconcentrated at reduced pressure
customto afford a dark yellow crystalline solid
customThe crude product was recrystallized from hexane

Sources & evidence

ORD record: ord-f7c4370264ef4afa9c17b83d3ff7a798
Source dataset: uspto-grants-1991_03
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US05001126

Linked notes

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