Benzyl Alcohol → 1-Benzoyl-5-methoxy-2-methylindole-3-acetic acid

HRID 863621Notes

Reaction equation

HRID 863621 reaction equation
C(OC1C2C(=CC=C(OC)C=2C)NC=1C)(=O)C.[Na].[CH2:19]([OH:26])[C:20]1[CH:25]=[CH:24][CH:23]=[CH:22][CH:21]=1.C([CH:34]([C:38]1[C:46]2[C:41](=[CH:42][CH:43]=[C:44]([O:47][CH3:48])[CH:45]=2)[NH:40][C:39]=1[CH3:49])[C:35]([O-:37])=[O:36])C1C=CC=CC=1>>[C:19]([N:40]1[C:41]2[C:46](=[CH:45][C:44]([O:47][CH3:48])=[CH:43][CH:42]=2)[C:38]([CH2:34][C:35]([OH:37])=[O:36])=[C:39]1[CH3:49])(=[O:26])[C:20]1[CH:25]=[CH:24][CH:23]=[CH:22][CH:21]=1

Participants

5

Reactant 4

HCID 244Benzyl AlcoholHCID 5360545SodiumHCID 19696995HCID 19696995, compoundHCID 54121235HCID 54121235, compound

Product 1

HCID 41779571-Benzoyl-5-methoxy-2-methylindole-3-acetic acid

Procedure

A solution of 15 g. of methyl-(2-methyl-5-methoxy-3-indolyl) acetate and 0.2 g. of sodium in 60 ml. of benzyl alcohol is slowly fractionated over a period of 41/2 hours through a Vigreux column to remove methanol. The excess benzyl alcohol is then removed by distillation at 60° C. (2.5 mm.) to give a residue of 18.6 g. of benzyl-(2-methyl-5-methoxy-3-indolyl)-acetate.

Workup

  1. customto remove methanol
  2. customThe excess benzyl alcohol is then removed by distillation at 60° C. (2.5 mm.)
  3. customto give a residue of 18.6 g

Sources & evidence

ORD record
ord-e65db01675c440569f63e4e9de8f6ff7
Source dataset
uspto-grants-1998_02
Patent number
US05721347

Reaction notes

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