Hydrochloric Acid → 4-[1-(2',4'-Dichloro-4-ethylbiphenyl-3-yl)-methylidene]-2,2,5,5-tetramethyldihydrofuran-3-one

HRID 879083Notes

Reaction equation

HRID 879083 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+].[Cl:14][C:15]1[CH:20]=[C:19]([Cl:21])[CH:18]=[CH:17][C:16]=1[C:22]1[CH:27]=[CH:26][C:25]([CH2:28][CH3:29])=[C:24]([CH:30]=O)[CH:23]=1.Cl>COCCOC>[Cl:14][C:15]1[CH:20]=[C:19]([Cl:21])[CH:18]=[CH:17][C:16]=1[C:22]1[CH:27]=[CH:26][C:25]([CH2:28][CH3:29])=[C:24]([CH:30]=[C:5]2[C:4]([CH3:9])([CH3:8])[O:3][C:2]([CH3:10])([CH3:1])[C:6]2=[O:7])[CH:23]=1

Participants

6

Reactant 4

HCID 313Hydrochloric AcidHCID 1385112,2,5,5-Tetramethyltetrahydro-3-ketofuranHCID 10942334Sodium MethoxideHCID 866636742',4'-Dichloro-4-ethylbiphenyl-3-carbaldehyde

Product 1

HCID 668237254-[1-(2',4'-Dichloro-4-ethylbiphenyl-3-yl)-methylidene]-2,2,5,5-tetramethyldihydrofuran-3-one

Reagents, catalysts & solvents 1

HCID 80711,2-DimethoxyethaneSolvent2×

Procedure

To an ice-cold solution of 2,2,5,5-tetramethyldihydrofuran-3-one (1.15 g, 0.0081 mol) in 1,2-dimethoxyethane (2 ml) is added sodium methoxide (0.481 g, 0.0089 mol) in one portion. The reaction mixture is then stirred for 5 minutes at this temperature, followed by the addition of a second solution of 2′,4′-dichloro-4-ethylbiphenyl-3-carbaldehyde (2.02 g, 0.0072 mol) in 1,2-dimethoxyethane (2.7 ml). After stirring for an additional 2 hours at 0° C. the reaction mixture is allowed to stand at room temperature overnight. The crude solution is poured into 2M hydrochloric acid and extracted with ether (×3). The organics are combined, washed with brine, dried over magnesium sulfate and concentrated in vacuo. The residue is purified by flash column chromatography (5% ethyl acetate in isohexane to 25% ethyl acetate in isohexane) to afford 4-[1-(2′,4′-dichloro-4-ethylbiphenyl-3-yl)-methylidene]-2,2,5,5-tetramethyldihydrofuran-3-one as a yellow gum.

Workup

  1. stirringAfter stirring for an additional 2 hours at 0° C. the reaction mixture
  2. waitto stand at room temperature overnight
  3. extractionextracted with ether (×3)
  4. washwashed with brine
  5. dry with materialdried over magnesium sulfate
  6. concentrationconcentrated in vacuo
  7. customThe residue is purified by flash column chromatography (5% ethyl acetate in isohexane to 25% ethyl acetate in isohexane)

Sources & evidence

ORD record
ord-028ebb4ef2cf4bf6b0992633fabf0fc0
Source dataset
uspto-grants-2015_03
Patent number
US08987476B2

Reaction notes

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