1-Benzyl-2-ethyl-4-methoxy-1H-indole → 1-Benzyl-2-ethyl-1H-indol-4-OL

HRID 396579Notes

Reaction equation

HRID 396579 reaction equation
[CH2:1]([C:3]1[N:4]([CH2:14][C:15]2[CH:20]=[CH:19][CH:18]=[CH:17][CH:16]=2)[C:5]2[C:10]([CH:11]=1)=[C:9]([O:12]C)[CH:8]=[CH:7][CH:6]=2)[CH3:2].B(Br)(Br)Br.C(Cl)Cl>>[CH2:1]([C:3]1[N:4]([CH2:14][C:15]2[CH:20]=[CH:19][CH:18]=[CH:17][CH:16]=2)[C:5]2[C:10]([CH:11]=1)=[C:9]([OH:12])[CH:8]=[CH:7][CH:6]=2)[CH3:2]

Participants

3

Reactant 2

HCID 99432411-Benzyl-2-ethyl-4-methoxy-1H-indoleHCID 22277759Boron tribromide dichloromethane

Product 1

HCID 98164161-Benzyl-2-ethyl-1H-indol-4-OLYield 54%

Procedure

3.1 g (11.7 mmol) of 2-ethyl-4-methoxy-1-(phenylmethyl)-1H-indole is O-demethylated by treating it with 48.6 mL of 1M BBr3/CH2Cl2, then stirred at room temperature for 5 hours and concentrated at reduced pressure. The residue is dissolved in ethyl acetate, then washed with brine and dried. The reaction product is then chromatographed on silica gel (eluted with 20% EtOAc/hexane) to give 1.58 g (54% yield) of 2-ethyl-4-hydroxy-1-(phenylmethyl)-1H-indole, mp, 86-90° C.

Workup

  1. concentrationconcentrated at reduced pressure
  2. dissolutionThe residue is dissolved in ethyl acetate
  3. washwashed with brine
  4. customdried
  5. customThe reaction product is then chromatographed on silica gel (eluted with 20% EtOAc/hexane)

Sources & evidence

ORD record
ord-ac33864194ec4bb5b4635ead8d3e806c
Source dataset
uspto-grants-2003_08
Patent number
US06608099B1

Reaction notes

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