Sodium hydride → HCID 69209868, compound

HRID 2251326Notes

Reaction equation

HRID 2251326 reaction equation
[Cl:1][C:2]1[CH:7]=[CH:6][CH:5]=[C:4]([Cl:8])[C:3]=1[C:9]1[C:13]([CH2:14][OH:15])=[C:12]([CH:16]([CH3:18])[CH3:17])[O:11][N:10]=1.[H-].[Na+].F[C:22]1[CH:23]=[CH:24][C:25]([N+:29]([O-:31])=[O:30])=[C:26]([CH3:28])[CH:27]=1>CN(C)C=O>[Cl:8][C:4]1[CH:5]=[CH:6][CH:7]=[C:2]([Cl:1])[C:3]=1[C:9]1[C:13]([CH2:14][O:15][C:22]2[CH:23]=[CH:24][C:25]([N+:29]([O-:31])=[O:30])=[C:26]([CH3:28])[CH:27]=2)=[C:12]([CH:16]([CH3:18])[CH3:17])[O:11][N:10]=1

Participants

5

Reactant 3

HCID 24758Sodium hydrideHCID 949565-Fluoro-2-nitrotolueneHCID 10850745(3-(2,6-Dichlorophenyl)-5-isopropylisoxazol-4-yl)methanol

Product 1

HCID 69209868HCID 69209868, compound

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

A solution of [3-(2,6-dichlorophenyl)-5-isopropylisoxazol-4-yl]methanol (500 mg, 1.79 mmol) in dimethylformamide (6 mL) at 0° C. was treated with sodium hydride (60% dispersion in oil, 72 mg, 1.8 mmol) and was maintained for 15 minutes before the addition of 5-fluoro-2-nitrotoluene (182 μL, 1.5 mmol). The reaction was then allowed to stir at ambient temperature for 16 h. The product was extracted by partitioning the mixture in diethyl ether (50 mL) and water (50 mL). The aqueoues phase was extracted with diethyl ether (3×50 mL) then the organics were combined and washed with brine (50 mL), dried over anhydrous magnesium sulfate, filtered and and concentrated to yield a crude oil. The product was purified by column chromatography on silica gel eluting with 20% ethyl acetate/hexanes. Yield=379 mg (60%) of 3-(2,6-dichlorophenyl)-5-isopropyl-4-[(3-methyl 4nitrophenoxy)methyl]-isoxazole.

Workup

  1. extractionThe product was extracted
  2. customby partitioning the mixture in diethyl ether (50 mL)
  3. extractionThe aqueoues phase was extracted with diethyl ether (3×50 mL)
  4. washwashed with brine (50 mL)
  5. dry with materialdried over anhydrous magnesium sulfate
  6. filtrationfiltered
  7. concentrationconcentrated
  8. customto yield a crude oil
  9. customThe product was purified by column chromatography on silica gel eluting with 20% ethyl acetate/hexanes

Sources & evidence

ORD record
ord-5d468231010b4401b01ce35fab329a94
Source dataset
uspto-grants-2008_01
Patent number
US07319109B2

Reaction notes

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