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

HRID 2212548Notes

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]

Participants

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

custom75% of the solvent were evaporated
additionthe resulting mixture was poured into 5 ml of water
extractionextracted with EtOAc
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-ba7b9d8b0040448e85904e4b0125ec39
Source dataset: uspto-grants-2006_09
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US07102007B2

Reaction notes

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