Diethyl Ether → HCID 54479667, compound

HRID 976539Notes

Reaction equation

HRID 976539 reaction equation
Br[C:2]1[CH:3]=[C:4]2[C:8](=[CH:9][CH:10]=1)[CH:7]([O:11][CH:12]1[CH2:17][CH2:16][CH2:15][CH2:14][O:13]1)[CH2:6][CH2:5]2.CCCCCC.C([Li])CCC.[CH2:29]([O:31]CC)C.[Cl-].[NH4+]>O1CCCC1>[CH:29]([C:2]1[CH:3]=[C:4]2[C:8](=[CH:9][CH:10]=1)[CH:7]([O:11][CH:12]1[CH2:17][CH2:16][CH2:15][CH2:14][O:13]1)[CH2:6][CH2:5]2)=[O:31]

Participants

6

Reactant 4

HCID 3283Diethyl EtherHCID 25517Ammonium ChlorideHCID 544859165-Bromo-1-(tetrahydropyran-2-yloxy)indaneHCID 178418244HCID 178418244, compound

Product 1

HCID 54479667HCID 54479667, compound

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

8.1 g of 5-bromo-1-(tetrahydropyran-2-yloxy)indane was dissolved in 100 ml of anhydrous tetrahydrofuran under a nitrogen atmosphere. To the solution was dropwise added 20 ml of a 1.5N n-butyllithiumhexan solution at -65° C. in 10 minutes. The resulting mixture was stirred at the same temperature for 5 minutes. Thereto was added 2.3 ml of anhydrous N,N-dimethylformaide. The reaction mixture was heated to room temperature and added to a mixture of 100 ml of ice water, 100 ml of diethyl ether and 2 g of ammonium chloride. The organic layer was separated, washed with water and a saturated aqueous sodium chloride solution in this order, 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 6.5 g of 5-formyl-1-(tetrahydropyran-2-yloxy)indane.

Workup

  1. customat -65° C.
  2. customin 10 minutes
  3. additionThereto was added 2.3 ml of anhydrous N,N-dimethylformaide
  4. customThe organic layer was separated
  5. washwashed with water
  6. dry with materiala saturated aqueous sodium chloride solution in this order, and dried over anhydrous magnesium sulfate
  7. customThe solvent was removed by distillation under reduced pressure
  8. customThe residue thus obtained
  9. customwas purified by column chromatography (eluant: toluene/ethyl acetate=15/1)

Sources & evidence

ORD record
ord-11343e8bce6f4ba0bbb569b6cb21cd80
Source dataset
uspto-grants-1997_03
Patent number
US05612381

Reaction notes

Loading…