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Sodium Hydroxide → 5-(6-Fluoro-1H-indol-5-yl)-pent-4-yn-1-ol

HRID 49514
Notes
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Reaction equation

HRID 49514 reaction equation
C(OC([N:8]1[C:16]2[C:11](=[CH:12][C:13]([C:18]#[C:19][CH2:20][CH2:21][CH2:22][OH:23])=[C:14]([F:17])[CH:15]=2)[CH:10]=[CH:9]1)=O)(C)(C)C.[OH-].[Na+]>CCO>[F:17][C:14]1[CH:15]=[C:16]2[C:11]([CH:10]=[CH:9][NH:8]2)=[CH:12][C:13]=1[C:18]#[C:19][CH2:20][CH2:21][CH2:22][OH:23]
ParticipantsConditionsProcedureWorkupSources & evidenceReaction notes

Participants

4

Reactant 2

HCID 14798Sodium HydroxideHCID 695149406-Fluoro-5-(5-hydroxy-pent-1-ynyl)-indole-1-carboxylic acid tert-butyl ester

Product 1

HCID 219666015-(6-Fluoro-1H-indol-5-yl)-pent-4-yn-1-olYield 843.9%

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Conditions

Temperature
60 °C

Procedure

A solution of 950 mg (0.3 mmol) 6-Fluoro-5-(5-hydroxy-pent-1-ynyl)-indole-1-carboxylic acid tert-butyl ester in 20 ml EtOH was treated with 2 ml of saturated aqeous NaOH and stirred during 2 hours at 60° C. 75% of the solvent were evaporated, the resulting mixture was poured into 5 ml of water, acidified with 2M aqueous HCl, and extracted with EtOAc. Drying of the combined organic layers with MgSO4, evaporation of the solvent, and chromatography on silica gel with CH2Cl2 gave 550 mg (84%) of 5-(6-Fluoro-1H-indol-5-yl)-pent-4-yn-1-ol as a viscous light yellow oil, MS: 218 (M).

Workup

  1. custom75% of the solvent were evaporated
  2. additionthe resulting mixture was poured into 5 ml of water
  3. extractionextracted with EtOAc
  4. dry with materialDrying of the combined organic layers with MgSO4, evaporation of the solvent, and chromatography on silica gel with CH2Cl2

Sources & evidence

ORD record
ord-cde321f9347c40b0841e0986ef021b4b
Source dataset
uspto-grants-2004_03
DOI
10.6084/m9.figshare.5104873.v1
Patent number
US06706751B2

Reaction notes

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On this pageParticipantsConditionsProcedureWorkupSources & evidenceReaction notes