1-Iodopropane → HCID 44549790, compound

HRID 2377061Notes

Reaction equation

HRID 2377061 reaction equation
[Na].[CH3:2][C:3]1[NH:4][O:5][C:6](=[O:13])[C:7]=1[C:8]([O:10][CH2:11][CH3:12])=[O:9].I[CH2:15][CH2:16][CH3:17]>CN(C=O)C>[CH3:2][C:3]1[N:4]([CH2:15][CH2:16][CH3:17])[O:5][C:6](=[O:13])[C:7]=1[C:8]([O:10][CH2:11][CH3:12])=[O:9]

Participants

4

Reactant 2

HCID 336431-IodopropaneHCID 69198820HCID 69198820, compound

Product 1

HCID 44549790HCID 44549790, compoundYield 13.5%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Conditions

Temperature
120 °C

Procedure

To a stirred solution of ethyl 3-methyl-5-oxo-2,5-dihydroisoxazole-4-carboxylate sodium salt [prepared according G. Doleschall, Tetrahedron Lett. 1987, 28, 2993-2994] (3.5 g, 18.1 mmol) in DMF (20 mL) was added 1-iodopropane (1.70 g, 18.1 mmol). The resulting mixture was heated to 120° C. for 1 hr. When cooled down, it was poured into ice-water (30 mL), and extracted with dichloromethane (2×50 mL). The organic layer was washed with water (2×50 mL), dried over sodium sulfate, concentrated and purified by flash chromatography with ethyl acetate/hexanes (1/1) to provide a solid product (0.52 g, 13% yield). 1H NMR (CDCl3) δ ppm 4.33 (q, 2H, J=7.1 Hz), 3.86 (t, 2H, J=6.8 Hz), 2.57 (s, 3H), 1.81-1.88 (m, 2H), 1.37 (t, 3H, J=7.1 Hz), 0.98 (t, 3H, J=7.6 Hz). LCMS (APCI, M+H+): 214.1.

Workup

  1. temperatureWhen cooled down
  2. extractionextracted with dichloromethane (2×50 mL)
  3. washThe organic layer was washed with water (2×50 mL)
  4. dry with materialdried over sodium sulfate
  5. concentrationconcentrated
  6. custompurified by flash chromatography with ethyl acetate/hexanes (1/1)

Sources & evidence

ORD record
ord-f41cdd2c417a4070b9240f44e52d250f
Source dataset
uspto-grants-2008_12
Patent number
US07468375B2

Reaction notes

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