HCID 23442874, compound → HCID 53674989, compound

HRID 2119695Notes

Reaction equation

HRID 2119695 reaction equation
[C:1]([C:5]1[CH:10]=[C:9]([O:11][C:12](=[O:17])[C:13]([CH3:16])([CH3:15])[CH3:14])[C:8]([C:18]([CH3:21])([CH3:20])[CH3:19])=[CH:7][C:6]=1[O:22]CC(C)=C)([CH3:4])([CH3:3])[CH3:2]>CN(C)C1C=CC=CC=1>[C:18]([C:8]1[C:7]2[CH2:2][C:1]([CH3:4])([CH3:3])[O:22][C:6]=2[C:5]([C:1]([CH3:2])([CH3:3])[CH3:4])=[CH:10][C:9]=1[O:11][C:12](=[O:17])[C:13]([CH3:15])([CH3:16])[CH3:14])([CH3:21])([CH3:19])[CH3:20]

Participants

3

Reactant 1

HCID 23442874HCID 23442874, compound

Product 1

HCID 53674989HCID 53674989, compoundYield 179.2%

Reagents, catalysts & solvents 1

HCID 949N,N-DimethylanilineSolvent

Procedure

Under a nitrogen stream, a solution of 0.48 g of 2,5-di-t-butyl-4-trimethylacetoxy-1-(2-methyl-2-propenyloxy)benzene in 5 ml of dimethylaniline was refluxed overnight. The solution was allowed to attain room temperature and concentrated under reduced pressure, then extracted with ethyl acetate and 5% hydrochloric acid. The organic layers were washed with saturated brine, dried over anhydrous magnesium sulfate, and then concentrated. The concentrate was purified by silica gel column chromatography (in n-hexane containing 0.5% ethyl acetate) to give 0.43 g of 4,7-di-t-butyl-2,2-dimethyl-5-trimethylacetoxy-2,3-dihydrobenzofuran as a colorless solid.

Workup

  1. customto attain room temperature
  2. concentrationconcentrated under reduced pressure
  3. extractionextracted with ethyl acetate and 5% hydrochloric acid
  4. washThe organic layers were washed with saturated brine
  5. dry with materialdried over anhydrous magnesium sulfate
  6. concentrationconcentrated
  7. customThe concentrate was purified by silica gel column chromatography (in n-hexane containing 0.5% ethyl acetate)

Sources & evidence

ORD record
ord-80f71d7b957540abb9abf7a24371f22e
Source dataset
uspto-grants-2004_02
Patent number
US06686389B2

Reaction notes

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