2,2,5,5-Tetramethyltetrahydro-3-ketofuran → HCID 66823581, compound

HRID 879060Notes

Reaction equation

HRID 879060 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]([I:23])=[C:19]([CH:22]=1)[CH:20]=O>COCCOC>[Br:14][C:15]1[CH:16]=[CH:17][C:18]([I: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

5

Reactant 3

HCID 1385112,2,5,5-Tetramethyltetrahydro-3-ketofuranHCID 10942334Sodium MethoxideHCID 219738615-Bromo-2-iodobenzaldehyde

Product 1

HCID 66823581HCID 66823581, compoundYield 99.3%

Reagents, catalysts & solvents 1

HCID 80711,2-DimethoxyethaneSolvent2×

Procedure

To an ice-cold solution of 2,2,5,5-tetramethyldihydrofuran-3-one (0.388 g, 2.73 mmoles) in anhydrous 1,2-dimethoxyethane (5 ml) is added sodium methoxide (0.177 g, 3.27 mmoles) in one portion. The reaction mixture is stirred for 5 minutes at this temperature, followed by the dropwise addition of 5-bromo-2-iodo-benzaldehyde (0.850 g, 2.73 mmoles) as a solution in 1,2-dimethoxyethane (5 ml). The reaction mixture is further stirred at 0° C. for 30 minutes, then at ambient temperature for a 1 hour. After partitioning between 1M hydrochloric acid and dichloromethane, the organic phase is separated, and the aqueous phase is extracted again with additional dichloromethane. All organics are combined then concentrated in vacuo to afford 4-[1-(5-bromo-2-iodophenyl)methylidene]-2,2,5,5-tetramethyldihydrofuran-3-one (1.18 g) as a yellow gum.

Workup

  1. stirringThe reaction mixture is further stirred at 0° C. for 30 minutes
  2. waitat ambient temperature for a 1 hour
  3. customAfter partitioning between 1M hydrochloric acid and dichloromethane
  4. customthe organic phase is separated
  5. extractionthe aqueous phase is extracted again with additional dichloromethane
  6. concentrationAll organics are combined then concentrated in vacuo

Sources & evidence

ORD record
ord-54b65d0f6126499f8b2e3bebf87f97c8
Source dataset
uspto-grants-2015_03
Patent number
US08987476B2

Reaction notes

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