3,4-dihydro-2H-pyran → HCID 21956075, compound

HRID 2246410Notes

Reaction equation

HRID 2246410 reaction equation
[Cl:1][C:2]1[NH:3][C:4]2[CH:10]=[C:9]([Cl:11])[C:8]([Cl:12])=[CH:7][C:5]=2[N:6]=1.[O:13]1[CH:18]=[CH:17][CH2:16][CH2:15][CH2:14]1.C12(CS(O)(=O)=O)C(C)(C)C(CC1)CC2=O.[OH-].[Na+]>O1CCCC1>[Cl:1][C:2]1[N:3]([CH:14]2[CH2:15][CH2:16][CH2:17][CH2:18][O:13]2)[C:4]2[CH:10]=[C:9]([Cl:11])[C:8]([Cl:12])=[CH:7][C:5]=2[N:6]=1

Participants

6

Reactant 4

HCID 80803,4-dihydro-2H-pyranHCID 14798Sodium HydroxideHCID 18462Bicyclo[2.2.1]heptane-1-methanesulfonic acid, 7,7-dimethyl-2-oxo-, (1S)-HCID 2860092,5,6-Trichloro-1H-benzimidazole

Product 1

HCID 21956075HCID 21956075, compoundYield 17.1%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

To a solution of 2,5,6-trichlorobenzimidazole (2.07 g, 9.33 mmol) in tetrahydrofuran (20 mL) were added 3,4-dihydro-2H-pyran (2.55 mL, 28.0 mmol) and camphor sulfonic acid (216 mg, 0.93 mmol). The mixture was stirred at room temperature for 3 hours, and the reaction mixture was neutralized by addition of 0.1M aqueous sodium hydroxide, then extracted with ethyl acetate. The organic layer was washed with saturated brine, dried over anhydrous sodium sulfate, and concentrated in vacuo. The residue was purified by silica gel column chromatography (C-300, hexane:ethyl acetate=4:1) to give the title compound (487 mg, 9%).

Workup

  1. extractionextracted with ethyl acetate
  2. washThe organic layer was washed with saturated brine
  3. dry with materialdried over anhydrous sodium sulfate
  4. concentrationconcentrated in vacuo
  5. customThe residue was purified by silica gel column chromatography (C-300, hexane:ethyl acetate=4:1)

Sources & evidence

ORD record
ord-c98bdd8bda23413bafa347abaa6b473d
Source dataset
uspto-grants-2010_03
Patent number
US07687514B2

Reaction notes

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