3,4-dihydro-2H-pyran → HCID 59838331, compound

HRID 2284482Notes

Reaction equation

HRID 2284482 reaction equation
[Br:1][C:2]1[C:7]([CH3:8])=[CH:6][C:5]([OH:9])=[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[C:7]([CH3:8])=[CH:6][C:5]([O:9][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 819704-Bromo-3,5-dimethylphenol

Product 1

HCID 59838331HCID 59838331, compoundYield 362.9%

Reagents, catalysts & solvents 2

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

Procedure

A mixture of 4-bromo-3,5-dimethylphenol (4.6 g, 22.88 mmol), 3,4 dihydro-2H-pyran (2.69 mL, 29.7 mmol) in 8.0 mL of CH2Cl2, and camphorsulfonic acid (106 mg, 4.56 mmol) was stirred at room temperature for 21 h. The reaction mixture was then quenched with equal volumes of 0.2 M NaOH and EtOAc (1:1, 20 mL) before the layers were separated. The water phase was further extracted with equal volume of EtOAc before the organic layers were combined and dried over anhydrous Na2SO4 and filtered. The solvent was removed under reduced pressure. The residue was purified by silica gel column using Combiflash to give 2-(4-bromo-3,5-dimethylphenoxy)tetrahydro-2H-pyran (23.68 g, 92%).

Workup

  1. customThe reaction mixture was then quenched with equal volumes of 0.2 M NaOH and EtOAc (1:1, 20 mL) before the layers
  2. customwere separated
  3. extractionThe water phase was further extracted with equal volume of EtOAc before the organic layers
  4. dry with materialdried over anhydrous Na2SO4
  5. filtrationfiltered
  6. customThe solvent was removed under reduced pressure
  7. customThe residue was purified by silica gel column

Sources & evidence

ORD record
ord-57dfa736db1a4b299b57e8b5bff93111
Source dataset
uspto-grants-2015_09
Patent number
US09145429B2

Reaction notes

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