Hydrochloric Acid → 4-[1-(4-Bromo-2-ethylphenyl)methylidene]-2,5-diethyl-2,5-dimethyldihydrofuran-3-one

HRID 341670Notes

Reaction equation

C[O-].[Na+].[CH2:4]([C:6]1([CH3:15])[C:10](=[O:11])[CH2:9][C:8]([CH2:13][CH3:14])([CH3:12])[O:7]1)[CH3:5].[Br:16][C:17]1[CH:24]=[CH:23][C:20]([CH:21]=O)=[C:19]([CH2:25][CH3:26])[CH:18]=1.Cl>C(COC)OC>[Br:16][C:17]1[CH:24]=[CH:23][C:20]([CH:21]=[C:9]2[C:8]([CH2:13][CH3:14])([CH3:12])[O:7][C:6]([CH2:4][CH3:5])([CH3:15])[C:10]2=[O:11])=[C:19]([CH2:25][CH3:26])[CH:18]=1

Participants

Conditions

Temperature: 0 °C

Procedure

Sodium methoxide (5.08 g, 0.094 mol) is added to a solution of 2,5-diethyl-2,5-dimethyldihydrofuran-3-one (8 g, 0.047 mol) in dimethoxyethane (40 ml) at 0° C. The reaction mixture is stirred for 15 minutes at 0° C. and a solution of 4-bromo-2-ethyl benzaldehyde (8.96 g, 0.042 mol) in dimethoxyethane (8 ml) is added. The reaction mixture is stirred at 0° C. for 1 hour, acidified to pH 1 with 2N aqueous hydrochloric acid and extracted with diethyl ether (3×75 ml). The organic phases are combined, washed with water, and dried over anhydrous sodium sulfate. The mixture is filtered, and the filtrate is evaporated under reduced pressure to give 4-[1-(4-bromo-2-ethylphenyl)methylidene]-2,5-diethyl-2,5-dimethyldihydrofuran-3-one (17 g), used without further purification in the next step.

Workup

stirringThe reaction mixture is stirred at 0° C. for 1 hour
extractionextracted with diethyl ether (3×75 ml)
washwashed with water
dry with materialdried over anhydrous sodium sulfate
filtrationThe mixture is filtered
customthe filtrate is evaporated under reduced pressure

Sources & evidence

ORD record: ord-ac1c56bbb5ce4727acd942e456f64655
Source dataset: uspto-grants-2014_11
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US08895761B2

Reaction notes

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