Methanol → 5-Benzyloxy-1-isopropyl-1H-indole-2-carboxylic acid

HRID 494004Notes

Reaction equation

HRID 494004 reaction equation
C([O:3][C:4]([C:6]1[N:7]([CH:23]([CH3:25])[CH3:24])[C:8]2[C:13]([CH:14]=1)=[CH:12][C:11]([O:15][CH2:16][C:17]1[CH:22]=[CH:21][CH:20]=[CH:19][CH:18]=1)=[CH:10][CH:9]=2)=[O:5])C.[OH-].[Li+].O.CO>O1CCCC1>[CH2:16]([O:15][C:11]1[CH:12]=[C:13]2[C:8](=[CH:9][CH:10]=1)[N:7]([CH:23]([CH3:25])[CH3:24])[C:6]([C:4]([OH:5])=[O:3])=[CH:14]2)[C:17]1[CH:22]=[CH:21][CH:20]=[CH:19][CH:18]=1

Participants

6

Reactant 4

HCID 887MethanolHCID 962WaterHCID 3939Lithium HydroxideHCID 670735335-Benzyloxy-1-isopropyl-1H-indole-2-carboxylic acid ethyl ester

Product 1

HCID 577407955-Benzyloxy-1-isopropyl-1H-indole-2-carboxylic acidYield 96%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

5-Benzyloxy-1-isopropyl-1H-indole-2-carboxylic acid ethyl ester (47.5 g, 1.0 eq.) and lithium hydroxide (6.56 g, 1.1 eq.) in a mixture of tetrahydofuran (360 mL), water (180 mL) and methanol (120 mL) was refluxed for 2 h then the reaction mixture was concentrated in vacuo. The residue was stirred vigorously in aqueous hydrochloric acid (2N, final pH: 2). The white precipitate was filtered, washed with water then dried in vacuo to yield 41.6 g (96%) of the desired product as white oil. MS (m/e): 308.5 (M−H, 100%).

Workup

  1. temperaturewas refluxed for 2 h
  2. concentrationthe reaction mixture was concentrated in vacuo
  3. filtrationThe white precipitate was filtered
  4. washwashed with water
  5. customthen dried in vacuo

Sources & evidence

ORD record
ord-52eb73305cce44d4897f0c232aaf366e
Source dataset
uspto-grants-2009_05
Patent number
US07538101B2

Reaction notes

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