2,2,5,5-Tetramethyltetrahydro-3-ketofuran → HCID 66823734, compound

HRID 1193247Notes

Reaction equation

HRID 1193247 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]([O:23][CH:24]([F:26])[F:25])=[C:19]([CH:22]=1)[CH:20]=O>COCCOC.CCOCC>[Br:14][C:15]1[CH:16]=[CH:17][C:18]([O:23][CH:24]([F:25])[F:26])=[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

6

Reactant 3

HCID 1385112,2,5,5-Tetramethyltetrahydro-3-ketofuranHCID 20641365-bromo-2-(difluoromethoxy)benzaldehydeHCID 10942334Sodium Methoxide

Product 1

HCID 66823734HCID 66823734, compoundYield 103%

Reagents, catalysts & solvents 2

HCID 3283Diethyl EtherSolventHCID 80711,2-DimethoxyethaneSolvent2×

Conditions

Temperature
0 °C

Procedure

To an ice-cold solution of 2,2,5,5-tetramethyldihydrofuran-3-one (3.60 g, 0.025 mol) in anhydrous 1,2-dimethoxyethane (8 ml) is added sodium methoxide (1.51 g, 0.028 mol) in one portion. After stirring at this temperature for 5 minutes a solution of 5-bromo-2-difluoromethoxy-benzaldehyde (5.66 g, 0.023 mol) in 1,2-dimethoxyethane (8 ml) is added dropwise over 10 mins, followed by stirring at 0° C. for a further 1 hour. After warming to room temperature the reaction mixture is diluted with ether and washed with 2M hydrochloric acid (×2). Organic fractions are combined, dried over magnesium sulfate and evaporated in vacuo to afford 4-[1-(5-bromo-2-difluoromethoxyphenyl)methylidene]-2,2,5,5-tetramethyldihydrofuran-3-one (8.89 g) as an orange oil.

Workup

  1. additionis added dropwise over 10 mins
  2. temperatureAfter warming to room temperature the reaction mixture
  3. washwashed with 2M hydrochloric acid (×2)
  4. dry with materialdried over magnesium sulfate
  5. customevaporated in vacuo

Sources & evidence

ORD record
ord-28d1fc103ffc4a28b9b722e0493b054c
Source dataset
uspto-grants-2014_03
Patent number
US08680299B2

Reaction notes

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