Methyl iodide → HCID 18696252, compound

HRID 1870296Notes

Reaction equation

HRID 1870296 reaction equation
[C:1]([O:5][C:6]([NH:8][CH2:9][CH2:10][O:11][C:12]1[C:16]2[CH:17]=[CH:18][CH:19]=[C:20]([CH3:21])[C:15]=2[O:14][N:13]=1)=[O:7])([CH3:4])([CH3:3])[CH3:2].[CH2:22]([Li])CCC.CI>O1CCCC1>[C:1]([O:5][C:6]([NH:8][CH2:9][CH2:10][O:11][C:12]1[C:16]2[C:17]([CH3:22])=[CH:18][CH:19]=[C:20]([CH3:21])[C:15]=2[O:14][N:13]=1)=[O:7])([CH3:4])([CH3:3])[CH3:2]

Participants

5

Reactant 3

HCID 6328Methyl iodideHCID 15453951HCID 15453951, compoundHCID 178418339Butyllithium

Product 1

HCID 18696252HCID 18696252, compoundYield 80%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Conditions

Temperature
-70 °C

Procedure

To a solution of 3-(2-(N-t-butoxycarbonylamino)ethoxy)-7-methyl-1,2-benzisoxazole (0.15 g) in tetrahydrofuran (5 ml) was added butyl lithium (0.7 ml, 1.6M hexane solution) dropwise with stirring at -70° C. under nitrogen atmosphere, the mixture was stirred at the same temperature for 10 minutes, and then the temperature was raised to 0° C. After cooling the reaction mixture to -70° C., methyl iodide (0.11 g) was added and the temperature was allowed to rise to 0° C. The reaction mixture was poured into ice water (40 ml), extracted with ethyl acetate (twice each with 40 ml) and the combined extracts were dried over anhydrous magnesium sulphate and filtered. The solvent was evaporated under reduced pressure and the residue was purified by silica gel column chromatography with cyclohexane/ethyl acetate (9/1) as an eluent, to give the title compound (0.12 g, 80%) as a colorless powder.

Workup

  1. stirringthe mixture was stirred at the same temperature for 10 minutes
  2. temperaturethe temperature was raised to 0° C
  3. temperatureAfter cooling the reaction mixture to -70° C.
  4. customto rise to 0° C
  5. extractionextracted with ethyl acetate (twice each with 40 ml) and the combined extracts
  6. dry with materialwere dried over anhydrous magnesium sulphate
  7. filtrationfiltered
  8. customThe solvent was evaporated under reduced pressure
  9. customthe residue was purified by silica gel column chromatography with cyclohexane/ethyl acetate (9/1) as an eluent

Sources & evidence

ORD record
ord-16d72d8b03ce45ac9bcdc0f29b6eb40a
Source dataset
uspto-grants-2000_08
Patent number
US06096771

Reaction notes

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