Sodium hydride → 5-allyloxy-N-neopentylindole

HRID 1275138Notes

Reaction equation

HRID 1275138 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-8d4340160ff04dc793a528bdda82125c
Source dataset
uspto-grants-2000_12
Patent number
US06160000

Reaction notes

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