Sodium hydride → 5-allyloxy-N-neopentylindole

HRID 2288890Notes

Reaction equation

HRID 2288890 reaction equation
[H-].[Na+].[CH2:3]([O:6][C:7]1[CH:8]=[C:9]2[C:13](=[CH:14][CH:15]=1)[NH:12][CH:11]=[CH:10]2)[CH:4]=[CH2:5].[CH2:16](I)[C:17]([CH3:20])([CH3:19])[CH3:18]>O1CCCC1>[CH2:3]([O:6][C:7]1[CH:8]=[C:9]2[C:13](=[CH:14][CH:15]=1)[N:12]([CH2:16][C:17]([CH3:20])([CH3:19])[CH3:18])[CH:11]=[CH:10]2)[CH:4]=[CH2:5]

Participants

5

Reactant 3

HCID 24758Sodium hydrideHCID 84953Propane, 1-iodo-2,2-dimethyl-HCID 142392305-(prop-2-en-1-yloxy)-1H-indole

Product 1

HCID 186724605-allyloxy-N-neopentylindole

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent2×

Procedure

To a solution of sodium hydride (60%, 254 mg, 6.35 mmol) in 15 mL tetrahydrofuran (THF) was added 5-allyloxyindole (Step A; 1.0 g, 5.77 mmol) in 5 mL THF and the mixture was stirred for 1 hour at ambient temperature. Neopentyl iodide (0.69 mL, 6.35 mmol) was added and the reaction heated to reflux for 21 hours. After cooling, the reaction was quenched with saturated aqueous ammonium chloride and extracted with ethyl acetate. The organic layer was washed with water, brine, dried over magnesium sulfate, filtered, concentrated in vacuo, and the crude residue purified by flash chromatography on silica gel (15% ethyl acetate/hexane) to provide the title compound.

Workup

  1. temperaturethe reaction heated
  2. temperatureto reflux for 21 hours
  3. temperatureAfter cooling
  4. customthe reaction was quenched with saturated aqueous ammonium chloride
  5. extractionextracted with ethyl acetate
  6. washThe organic layer was washed with water, brine
  7. dry with materialdried over magnesium sulfate
  8. filtrationfiltered
  9. concentrationconcentrated in vacuo
  10. customthe crude residue purified by flash chromatography on silica gel (15% ethyl acetate/hexane)

Sources & evidence

ORD record
ord-8663cd9c3673474b93afebee0a5deb09
Source dataset
uspto-grants-2000_07
Patent number
US06090839

Reaction notes

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