HCID 23442874, compound → HCID 53674989, compound

HRID 2186267Notes

Reaction equation

HRID 2186267 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-48f7cdf4de0247d59605021c05aa3532
Source dataset
uspto-grants-2002_06
Patent number
US06403639B1

Reaction notes

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