N-Iodosuccinimide → Methyl 4-iodo-5-isobutylisoxazole-3-carboxylate

HRID 1506321Notes

Reaction equation

HRID 1506321 reaction equation
[CH2:1]([C:5]1[O:9][N:8]=[C:7]([C:10]([O:12][CH3:13])=[O:11])[CH:6]=1)[CH:2]([CH3:4])[CH3:3].[I:14]N1C(=O)CCC1=O>C(O)(C(F)(F)F)=O>[I:14][C:6]1[C:7]([C:10]([O:12][CH3:13])=[O:11])=[N:8][O:9][C:5]=1[CH2:1][CH:2]([CH3:4])[CH3:3]

Participants

4

Reactant 2

HCID 120273N-IodosuccinimideHCID 3477558Methyl 5-isobutylisoxazole-3-carboxylate

Product 1

HCID 58374143Methyl 4-iodo-5-isobutylisoxazole-3-carboxylateYield 78%

Reagents, catalysts & solvents 1

HCID 6422Trifluoroacetic acidSolvent

Procedure

A mixture of methyl 5-isobutylisoxazole-3-carboxylate (Preparation 5A, 0.923 g, 5.04 mmol) and N-iodosuccinimide (1.247 g, 5.54 mmol) in TFA (25 mL) was stirred at room temperature overnight. The TFA was removed under reduced pressure, and the residue was diluted with dichloromethane (100 mL), washed with a saturated aqueous solution of sodium bicarbonate (2×25 mL), 2.5% aqueous solution of sodium bisulfate (25 mL), and dried over anhydrous sodium sulfate. Concentration under reduced pressure followed by purification by flash silica gel chromatography using a 5% mixture of ethyl acetate in hexane afforded methyl 4-iodo-5-isobutylisoxazole-3-carboxylate (1.21 g, 3.91 mmol, 78% yield) as a pale yellow oil. The product had an HPLC ret. time=2.40 min. (condition A); LC/MS M+1=310.1.

Workup

  1. customThe TFA was removed under reduced pressure
  2. additionthe residue was diluted with dichloromethane (100 mL)
  3. washwashed with a saturated aqueous solution of sodium bicarbonate (2×25 mL), 2.5% aqueous solution of sodium bisulfate (25 mL)
  4. dry with materialdried over anhydrous sodium sulfate
  5. concentrationConcentration under reduced pressure
  6. customfollowed by purification by flash silica gel chromatography

Sources & evidence

ORD record
ord-9ba6f2216a3043f59cff1cef6078e271
Source dataset
uspto-grants-2015_12
Patent number
US09216972B2

Reaction notes

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