1,2-Dichlorobenzene → 4-allyl-5-hydroxy-N-neopentylindole

HRID 1275139Notes

Reaction equation

HRID 1275139 reaction equation
C([O:4][C:5]1[CH:6]=[C:7]2[C:11](=[CH:12][CH:13]=1)[N:10]([CH2:14][C:15]([CH3:18])([CH3:17])[CH3:16])[CH:9]=[CH:8]2)C=C.Cl[C:20]1[CH:25]=CC=C[C:21]=1Cl>>[CH2:25]([C:6]1[C:5]([OH:4])=[CH:13][CH:12]=[C:11]2[C:7]=1[CH:8]=[CH:9][N:10]2[CH2:14][C:15]([CH3:16])([CH3:17])[CH3:18])[CH:20]=[CH2:21]

Participants

3

Reactant 2

HCID 72391,2-DichlorobenzeneHCID 186724605-allyloxy-N-neopentylindole

Product 1

HCID 186724644-allyl-5-hydroxy-N-neopentylindole

Procedure

5-Allyloxy-N-neopentylindole (Step B; 1.4 g, 4.93 mmol) was refluxed in 20 mL 1,2-dichlorobenzene for 4 hours. The reaction mixture was cooled and immediately purified by flash chromatography on silica gel (gradient elution: hexane then 10% ethyl acetate/hexane) to provide the title compound.

Workup

  1. temperatureThe reaction mixture was cooled
  2. customimmediately purified by flash chromatography on silica gel (
  3. washgradient elution

Sources & evidence

ORD record
ord-57f5930507a44284a3340a3522f8faa6
Source dataset
uspto-grants-2000_12
Patent number
US06160000

Reaction notes

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