3,4-dihydro-2H-pyran → HCID 22408116, compound

HRID 439786Notes

Reaction equation

HRID 439786 reaction equation
[Br:1][C:2]1[CH:9]=[CH:8][C:5]([CH2:6][OH:7])=[CH:4][C:3]=1[CH3:10].[O:11]1[CH:16]=[CH:15][CH2:14][CH2:13][CH2:12]1>C(Cl)Cl.C12(CS(O)(=O)=O)C(C)(C)C(CC1)CC2=O>[Br:1][C:2]1[CH:9]=[CH:8][C:5]([CH2:6][O:7][CH:12]2[CH2:13][CH2:14][CH2:15][CH2:16][O:11]2)=[CH:4][C:3]=1[CH3:10]

Participants

5

Reactant 2

HCID 80803,4-dihydro-2H-pyranHCID 10987288(4-Bromo-3-methylphenyl)methanol

Product 1

HCID 22408116HCID 22408116, compoundYield 100%

Reagents, catalysts & solvents 2

HCID 18462Bicyclo[2.2.1]heptane-1-methanesulfonic acid, 7,7-dimethyl-2-oxo-, (1S)-CatalystHCID 6344DichloromethaneSolvent2×

Procedure

4-bromo-3-methylbenzyl alcohol (2 g, 0.01 mol) was dissolved in methylene chloride (10 ml). Under ice-cooling, to the obtained solution was added 3,4-dihydropyran (1 ml, 0.011 mol) and 10-camphorsulfonic acid (120 mg, 0.5 millimol), and the mixture was stirred at room temperature for 1.5 hours. After diluting with methylene chloride, the mixture was washed with saturated aqueous sodium hydrogencarbonate solution, water and saturated aqueous sodium chloride solution. After drying over anhydrous sodium sulfate, the solvent was distilled away, and the residue was separated and purified by using a silica-gel column chromatography (ethyl acetatee:n-hexane=1:3) to give the title compound (2.8 g, 0.01 mol).

Workup

  1. temperatureUnder ice-cooling, to the obtained solution
  2. washthe mixture was washed with saturated aqueous sodium hydrogencarbonate solution, water and saturated aqueous sodium chloride solution
  3. dry with materialAfter drying over anhydrous sodium sulfate
  4. distillationthe solvent was distilled away
  5. customthe residue was separated
  6. custompurified

Sources & evidence

ORD record
ord-523a5183a6b4452e830f81ff6dd9b353
Source dataset
uspto-grants-1996_05
Patent number
US05516777

Reaction notes

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