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

HRID 2304630Notes

Reaction equation

HRID 2304630 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 is stirred at room temperature for 5 hours and concentrated at reduced pressure. The residue is dissolved in ethyl acetate, washed with brine and dried (MgSO4). After concentrating at reduced pressure, the residue is 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 is dissolved in ethyl acetate
  3. washwashed with brine
  4. dry with materialdried (MgSO4)
  5. concentrationAfter concentrating at reduced pressure
  6. customthe residue is chromatographed on silica gel eluting with 20% EtOAc/hexane

Sources & evidence

ORD record
ord-90fb9e956ed64e7cad6b41ebea55b07c
Source dataset
uspto-grants-2002_08
Patent number
US06436983B1

Reaction notes

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