2,2,5,5-Tetramethyltetrahydro-3-ketofuran → HCID 66823613, compound

HRID 1193226Notes

Reaction equation

HRID 1193226 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:20]=[CH:19][C:18]([C:21]2[CH:26]=[CH:25][C:24]([Cl:27])=[CH:23][CH:22]=2)=[CH:17][C:16]=1[CH:28]=O>COCCOC>[Br:14][C:15]1[CH:20]=[CH:19][C:18]([C:21]2[CH:26]=[CH:25][C:24]([Cl:27])=[CH:23][CH:22]=2)=[CH:17][C:16]=1[CH:28]=[C:5]1[C:4]([CH3:9])([CH3:8])[O:3][C:2]([CH3:10])([CH3:1])[C:6]1=[O:7]

Participants

5

Reactant 3

HCID 1385112,2,5,5-Tetramethyltetrahydro-3-ketofuranHCID 10942334Sodium MethoxideHCID 86663664HCID 86663664, compound

Product 1

HCID 66823613HCID 66823613, compoundYield 92%

Reagents, catalysts & solvents 1

HCID 80711,2-DimethoxyethaneSolvent2×

Procedure

To an ice-cold solution of dihydro-2,2,5,5-tetramethylfuran-3-one (1.37 g (9.68 mmol) in anhydrous 1,2-dimethoxyethane (10 ml) is added sodium methoxide (0.575 g, 10.60 mmol) in one portion, followed by stirring at this temperature for 10 minutes. To this slurry is then added a second solution of 4-bromo-4′-chloro-biphenyl-3-carbaldehyde (2.60 g, 8.80 mmol) in 1,2-dimethoxyethane (10 ml) dropwise. When addition is complete the reaction mixture is stirred at 0° C. for a further 1 hour, then quenched with 2M hydrochloric acid (50 ml). After stirring for an additional 1 hour the solution is diluted with diethyl ether, the two phases separated, and the aqueous phase further extracted with diethyl ether (×2). The combined organics are further washed with brine, then dried over magnesium sulfate, filtered, and the filtrate concentrated in vacuo to afford 4-[1-(4-bromo-4′-chlorobiphenyl-3-yl)-methylidene]-2,2,5,5-tetramethyldihydrofuran-3-one (3.40 g, 92%) as a yellow gum.

Workup

  1. additionWhen addition
  2. stirringis stirred at 0° C. for a further 1 hour
  3. customquenched with 2M hydrochloric acid (50 ml)
  4. stirringAfter stirring for an additional 1 hour the solution
  5. additionis diluted with diethyl ether
  6. customthe two phases separated
  7. extractionthe aqueous phase further extracted with diethyl ether (×2)
  8. washThe combined organics are further washed with brine
  9. dry with materialdried over magnesium sulfate
  10. filtrationfiltered
  11. concentrationthe filtrate concentrated in vacuo

Sources & evidence

ORD record
ord-3da8b0a9e9b84100afd216bdfc956437
Source dataset
uspto-grants-2014_03
Patent number
US08680299B2

Reaction notes

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