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

HRID 1280814Notes

Reaction equation

HRID 1280814 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>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

4

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%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

A solution of 3.1 g (11.7 mmol) of 2-ethyl-4-methoxy-1-(phenylmethyl)-1H-indole and 48.6 mL of 1M BBr3/CH2Cl2 in 50 mL of methylene chloride was stirred at room temperature for 5 hours and concentrated at reduced pressure. The residue was dissolved in ethyl acetate, washed with brine and dried (MgSO4). After concentrating at reduced pressure, the residue was chromatographed on silica gel eluting 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 was dissolved in ethyl acetate
  3. washwashed with brine
  4. dry with materialdried (MgSO4)
  5. concentrationAfter concentrating at reduced pressure
  6. customthe residue was chromatographed on silica gel eluting with 20% EtOAc/hexane

Sources & evidence

ORD record
ord-3dd8eb1bb81c4f82ba102f806f946f21
Source dataset
uspto-grants-2002_09
Patent number
US06451839B1

Reaction notes

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