Pivaloyl chloride → HCID 68428320, compound

HRID 384132Notes

Reaction equation

HRID 384132 reaction equation
[N+:1]([C:4]1[CH:5]=[C:6]([CH2:10][CH2:11][O:12][C:13]2[CH:18]=[CH:17][C:16]([C:19]3[O:23][N:22]=[C:21]([OH:24])[CH:20]=3)=[CH:15][CH:14]=2)[CH:7]=[CH:8][CH:9]=1)([O-:3])=[O:2].[C:25](Cl)(=[O:30])[C:26]([CH3:29])([CH3:28])[CH3:27]>C(Cl)(Cl)Cl.C(N(CC)CC)C.C(OCC)(=O)C>[C:25]([O:24][C:21]1[CH:20]=[C:19]([C:16]2[CH:15]=[CH:14][C:13]([O:12][CH2:11][CH2:10][C:6]3[CH:7]=[CH:8][CH:9]=[C:4]([N+:1]([O-:3])=[O:2])[CH:5]=3)=[CH:18][CH:17]=2)[O:23][N:22]=1)(=[O:30])[C:26]([CH3:29])([CH3:28])[CH3:27]

Participants

6

Reactant 2

HCID 62493Pivaloyl chlorideHCID 178526621HCID 178526621, compound

Product 1

HCID 68428320HCID 68428320, compound

Reagents, catalysts & solvents 3

HCID 6212ChloroformSolventHCID 8471TriethylamineSolventHCID 8857Ethyl AcetateSolvent

Procedure

To a solution of 5-(4-(2-(3-nitrophenyl)ethoxy)phenyl)isoxazol-3-ol (117 mg) obtained in Example 37 in chloroform (5 ml), 0.15 ml of triethylamine and 0.052 ml of pivaloyl chloride were added, and the reaction solution was stirred at room temperature for 2 hours. The reaction solution was diluted with ethyl acetate, washed with a saturated saline solution, and dried over anhydrous magnesium sulfate. The solvent was distilled off under reduced pressure, and the residue obtained was purified by silica gel column chromatography (eluent: ethyl acetate/hexane (0:1-1:3)) to afford the title compound as a white solid.

Workup

  1. washwashed with a saturated saline solution
  2. dry with materialdried over anhydrous magnesium sulfate
  3. distillationThe solvent was distilled off under reduced pressure
  4. customthe residue obtained
  5. customwas purified by silica gel column chromatography (eluent: ethyl acetate/hexane (0:1-1:3))

Sources & evidence

ORD record
ord-d8b52e62bec34da88dc43ea7135294be
Source dataset
uspto-grants-2013_02
Patent number
US08367708B2

Reaction notes

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