Tetrahydrofuran → HCID 67370826, compound

HRID 378799Notes

Reaction equation

HRID 378799 reaction equation
[H-].[Na+].C1COCC1.[Cl:8][C:9]1[CH:10]=[C:11]([OH:16])[CH:12]=[C:13]([Cl:15])[CH:14]=1.[Cl:17][C:18]1[CH:23]=[CH:22][C:21](Cl)=[N+:20]([O-:25])[C:19]=1[C:26]([O:28][CH3:29])=[O:27]>C(OCC)(=O)C.O>[Cl:17][C:18]1[CH:23]=[CH:22][C:21]([O:16][C:11]2[CH:10]=[C:9]([Cl:8])[CH:14]=[C:13]([Cl:15])[CH:12]=2)=[N+:20]([O-:25])[C:19]=1[C:26]([O:28][CH3:29])=[O:27]

Participants

7

Reactant 4

HCID 8028TetrahydrofuranHCID 115713,5-DichlorophenolHCID 24758Sodium hydrideHCID 86757459HCID 86757459, compound

Product 1

HCID 67370826HCID 67370826, compoundYield 76.5%

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 8857Ethyl AcetateSolvent

Procedure

To a dry 3-neck round bottom flask was added 60% NaH (0.432 g, 10.81 mmol), dry THF (30 mL) and 3,5-dichlorophenol (1.76 g, 10.81 mmol). The mixture was stirred until evolution of H2 (g) ceased. Methyl 3,6-dichloropyridine-2-carboxylate N-oxide (2.0 g, 9.00 mmol) was added in one portion and stirred at RT for 3 hr, diluted with ethyl acetate and 100 mL of water. The aqueous phase was extracted with ethyl acetate (2×200 mL). The combined extracts were dried (MgSO4) and concentrated to give 2.40 g of white solid.

Workup

  1. stirringstirred at RT for 3 hr
  2. extractionThe aqueous phase was extracted with ethyl acetate (2×200 mL)
  3. dry with materialThe combined extracts were dried (MgSO4)
  4. concentrationconcentrated

Sources & evidence

ORD record
ord-d3b99e60f65941178aaeb56059a0abb7
Source dataset
uspto-grants-2001_10
Patent number
US06297197B1

Reaction notes

Loading…