3,4-dihydro-2H-pyran → 5-Bromo-1-(tetrahydropyran-2-yloxy)indane

HRID 976538Notes

Reaction equation

HRID 976538 reaction equation
[Br:1][C:2]1[CH:3]=[C:4]2[C:8](=[CH:9][CH:10]=1)[CH:7]([OH:11])[CH2:6][CH2:5]2.C1(C)C=CC(S([O-])(=O)=O)=CC=1.[NH+]1C=CC=CC=1.[O:29]1[CH:34]=[CH:33][CH2:32][CH2:31][CH2:30]1>C(Cl)Cl>[Br:1][C:2]1[CH:3]=[C:4]2[C:8](=[CH:9][CH:10]=1)[CH:7]([O:11][CH:30]1[CH2:31][CH2:32][CH2:33][CH2:34][O:29]1)[CH2:6][CH2:5]2

Participants

5

Reactant 3

HCID 80803,4-dihydro-2H-pyranHCID 466102Benzenesulfonic acid, 4-methyl-, compd. with pyridine (1:1)HCID 134862995-bromo-2,3-dihydro-1H-inden-1-ol

Product 1

HCID 544859165-Bromo-1-(tetrahydropyran-2-yloxy)indane

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

9.6 g of 5-bromo-1-hydroxyindane was dissolved in 100 ml of dry methylene chloride. To the solution were added, at room temperature, 570 mg of pyridinium p-toluenesulfonate and 4.5 ml of 3,4-dihydro-2H-pyran. The resulting mixture was stirred at the same temperature for 3 hours. The reaction mixture was added to ice water. The organic layer was separated, washed with a saturated aqueous sodium chloride solution, and dried over anhydrous magnesium sulfate. The solvent was removed by distillation under reduced pressure. The residue thus obtained was purified by column chromatography (eluant: toluene/ethyl acetate=15/1) to obtain 13.1 g of oily 5-bromo-1-(tetrahydropyran-2-yloxy)indane.

Workup

  1. additionTo the solution were added, at room temperature
  2. customThe organic layer was separated
  3. washwashed with a saturated aqueous sodium chloride solution
  4. dry with materialdried over anhydrous magnesium sulfate
  5. customThe solvent was removed by distillation under reduced pressure
  6. customThe residue thus obtained
  7. customwas purified by column chromatography (eluant: toluene/ethyl acetate=15/1)

Sources & evidence

ORD record
ord-ba60fc2877584a77b8f62dc9fe8b12e5
Source dataset
uspto-grants-1997_03
Patent number
US05612381

Reaction notes

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