Sodium Chloride → 2,2-Dimethyl-5-[2-(3-thienyl)ethenyl]-3(2H)-furanone

HRID 359375Notes

Reaction equation

[S:1]1[CH:5]=[CH:4][C:3]([CH:6]=O)=[CH:2]1.[CH3:8][C:9]1([CH3:16])[C:13](=[O:14])[CH:12]=[C:11]([CH3:15])[O:10]1.[OH-].[Na+].[Cl-].[Na+]>C(O)C>[CH3:8][C:9]1([CH3:16])[C:13](=[O:14])[CH:12]=[C:11]([CH:15]=[CH:6][C:3]2[CH:4]=[CH:5][S:1][CH:2]=2)[O:10]1

Participants

Conditions

Temperature: 60 °C

Procedure

To a solution of 3-thiophenecarboxaldehyde (1.5 g, 13.2 mM) and 2,2,5-trimethyl-3(2H)-furanone (1.5 g, 12 mM) in ethanol (100 mL), was added 1N aqueous sodium hydroxide (1.2 mL, 1.2 mM). the reaction solution heated to 60° C. for 4 hours. After the reaction solution cooled, saturated aqueous sodium chloride (400 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 yellow crystalline solid. The residue was purified by chromatography (silica gel, hexane/ethyl acetate) to yield yellow crystals (2.1 g, 72% yield), m.p. 79°-80° C.

Workup

temperatureAfter the reaction solution cooled
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 yellow crystalline solid
customThe residue was purified by chromatography (silica gel, hexane/ethyl acetate)

Sources & evidence

ORD record: ord-7cf75a47aa5443c4b7d20c07ee9ed2e8
Source dataset: uspto-grants-1991_03
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US05001126

Reaction notes

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