Potassium Iodide → HCID 22506832, compound

HRID 985584Notes

Reaction equation

HRID 985584 reaction equation
[C:1]([C:5]1[C:13]2[O:12][C:11]([CH3:15])([CH3:14])[CH2:10][C:9]=2[C:8]([CH3:16])=[C:7]([NH:17]C(=O)OC(C)(C)C)[CH:6]=1)([CH3:4])([CH3:3])[CH3:2].[H-].[Na+].Cl[CH2:28][C:29]([CH3:31])=[CH2:30].[I-].[K+]>CN(C)C=O.CCCCCC>[C:1]([C:5]1[C:13]2[O:12][C:11]([CH3:14])([CH3:15])[CH2:10][C:9]=2[C:8]([CH3:16])=[C:7]([NH:17][CH2:30][C:29]([CH3:31])=[CH2:28])[CH:6]=1)([CH3:2])([CH3:3])[CH3:4]

Participants

7

Reactant 4

HCID 4875Potassium IodideHCID 112413-Chloro-2-methyl-1-propeneHCID 24758Sodium hydrideHCID 22506831HCID 22506831, compound

Product 1

HCID 22506832HCID 22506832, compoundYield 100.3%

Reagents, catalysts & solvents 2

HCID 6228DimethylformamideSolventHCID 8058HexaneSolvent

Procedure

tert-Butyl N-[7-(tert-butyl)-2,3-dihydro-2,2,4-trimethyl-1-benzofuran-5-yl]carbamate (7.17 g, 21.5 mmol) was dissolved in N,N-dimethylformamide (72 ml), and sodium hydride (0.62 g, 25.8 mmol) which had been washed with hexane was added at 0° C. carefully. After stirring at room temperature for 30 minutes, 3-chloro-2-methyl-1-propene (2.53 ml, 25.8 mmol) and potassium iodide (0.36 g, 2.2 mmol) were added and the mixture was stirred at the same temperature for 1 hour. The reaction mixture was washed with saturated brine and dried over sodium sulfate, and the solvent was removed under reduced pressure. The residue was purified by a column chromatography on a silica gel (hexane:ethyl acetate=4:1). The resultant oil was dissolved in methanol (85 ml), combined with concentrated hydrochloric acid (8.5 ml), and stirred under argon atmosphere at 50° C. for 2 hours. After cooling to 0° C., the mixture was made weakly basic using a 3N aqueous solution of sodium hydroxide, and extracted with ethyl acetate. The organic layer was washed with saturated brine, dried over sodium sulfate, and the solvent was removed under reduced pressure, and then crystallized from a cold hexane to obtain 6.20 g of the title compound.

Workup

  1. additionwas added at 0° C. carefully
  2. stirringthe mixture was stirred at the same temperature for 1 hour
  3. washThe reaction mixture was washed with saturated brine
  4. dry with materialdried over sodium sulfate
  5. customthe solvent was removed under reduced pressure
  6. customThe residue was purified by a column chromatography on a silica gel (hexane:ethyl acetate=4:1)
  7. dissolutionThe resultant oil was dissolved in methanol (85 ml)
  8. stirringstirred under argon atmosphere at 50° C. for 2 hours
  9. temperatureAfter cooling to 0° C.
  10. extractionextracted with ethyl acetate
  11. washThe organic layer was washed with saturated brine
  12. dry with materialdried over sodium sulfate
  13. customthe solvent was removed under reduced pressure
  14. customcrystallized from a cold hexane

Sources & evidence

ORD record
ord-6e7f4c5b065e424281f1391a27b4fcd3
Source dataset
uspto-grants-2005_03
Patent number
US06872718B1

Reaction notes

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