N,N-Dimethylaniline → HCID 86586188, compound

HRID 2119704Notes

Reaction equation

HRID 2119704 reaction equation
[C:1]([C:5]1[C:19]([O:20]CC=C)=[CH:18][C:8]2[CH2:9][C:10]3([O:17][C:7]=2[CH:6]=1)[CH2:16][CH2:15][CH2:14][CH2:13][CH2:12][CH2:11]3)([CH3:4])([CH3:3])[CH3:2].CN(C)[C:26]1[CH:31]=CC=C[CH:27]=1>>[C:1]([C:5]1[C:19]([OH:20])=[C:18]([CH2:31][CH:26]=[CH2:27])[C:8]2[CH2:9][C:10]3([O:17][C:7]=2[CH:6]=1)[CH2:16][CH2:15][CH2:14][CH2:13][CH2:12][CH2:11]3)([CH3:4])([CH3:2])[CH3:3]

Participants

3

Reactant 2

HCID 949N,N-DimethylanilineHCID 69890792HCID 69890792, compound

Product 1

HCID 86586188HCID 86586188, compoundYield 67%

Procedure

Under a nitrogen stream, a solution of 0.76 g of 6-t-butyl-5-(2-propenyloxy)-2,3-dihydrobenzofuran-2-spiro-1′-cycloheptane was dissolved in 3 ml of dimethylaniline and the solution was refluxed overnight. The reaction mixture was allowed to attain room temperature and concentrated under reduced pressure, then extracted with ethyl acetate and 5% hydrochloric acid and 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 1%-2% ethyl acetate) to give 0.51 g of 6-t-butyl-5-hydroxy-4-(2-propenyl)-2,3-dihydrobenzofuran-2-spiro-1′-cycloheptane as a colorless oil (yield 67%).

Workup

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

Sources & evidence

ORD record
ord-5ea4baaee4d740c280985c4b468cc358
Source dataset
uspto-grants-2004_02
Patent number
US06686389B2

Reaction notes

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