2,2,5,5-Tetramethyltetrahydro-3-ketofuran → HCID 66823601, compound

HRID 879069Notes

Reaction equation

[CH3:1][C:2]1([CH3:10])[C:6](=[O:7])[CH2:5][C:4]([CH3:9])([CH3:8])[O:3]1.C[O-].[Na+].[Br:14][C:15]1[CH:16]=[CH:17][C:18]([F:23])=[C:19]([CH:22]=1)[CH:20]=O>COCCOC>[Br:14][C:15]1[CH:16]=[CH:17][C:18]([F:23])=[C:19]([CH:20]=[C:5]2[C:4]([CH3:9])([CH3:8])[O:3][C:2]([CH3:10])([CH3:1])[C:6]2=[O:7])[CH:22]=1

Participants

Conditions

Temperature: 0 °C

Procedure

To an ice-cold solution of dihydro-2,2,5,5-tetramethylfuran-3-one (4.56 g, 32.10 mmol) in anhydrous 1,2-dimethoxyethane (25 ml) is added sodium methoxide (1.91 g, 35.10 mol) in one portion. After stirring at room temperature for 10 minutes a second solution of 5-bromo-2-fluorobenzaldehyde (5.93 g, 29.10 mmol) in anhydrous 1,2-dimethoxyethane (45 ml) is added dropwise, followed by stirring at 0° C. for a further 45 minutes. The reaction mixture is quenched with 2M hydrochloric acid (50 ml), then diluted with diethyl ether and the two phases separated. The aqueous phase is further extracted with diethyl ether (×2), then all organics are combined, washed with brine and dried over magnesium sulfate. After filtration the filtrate is concentrated in vacuo to afford 4-[1-(5-bromo-2-fluorophenyl)-methylidene]-2,2,5,5-tetramethyldihydrofuran-3-one (9.30 g, 96%) as a yellow gum.

Workup

additionis added dropwise
customThe reaction mixture is quenched with 2M hydrochloric acid (50 ml)
additiondiluted with diethyl ether
customthe two phases separated
extractionThe aqueous phase is further extracted with diethyl ether (×2)
washwashed with brine
dry with materialdried over magnesium sulfate
filtrationAfter filtration the filtrate
concentrationis concentrated in vacuo

Sources & evidence

ORD record: ord-3e881041c53841bc8a864ce3ce690865
Source dataset: uspto-grants-2015_03
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US08987476B2

Reaction notes

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