Lithium Hydroxide → HCID 22485675, compound

HRID 2181190Notes

Reaction equation

HRID 2181190 reaction equation
C([O:3][C:4](=[O:28])[CH:5]([O:24][CH2:25][CH2:26][CH3:27])[CH2:6][C:7]1[CH:8]=[C:9]2[C:13](=[CH:14][CH:15]=1)[N:12]([CH2:16][O:17][CH2:18][CH2:19][Si:20]([CH3:23])([CH3:22])[CH3:21])[CH:11]=[CH:10]2)C.[OH-].[Li+]>O1CCOCC1>[CH2:25]([O:24][CH:5]([CH2:6][C:7]1[CH:8]=[C:9]2[C:13](=[CH:14][CH:15]=1)[N:12]([CH2:16][O:17][CH2:18][CH2:19][Si:20]([CH3:23])([CH3:21])[CH3:22])[CH:11]=[CH:10]2)[C:4]([OH:28])=[O:3])[CH2:26][CH3:27]

Participants

4

Reactant 2

HCID 3939Lithium HydroxideHCID 69563406HCID 69563406, compound

Product 1

HCID 22485675HCID 22485675, compoundYield 85.6%

Reagents, catalysts & solvents 1

HCID 312751,4-DioxaneSolvent

Procedure

1.23 g rac-2-propoxy-3-[1-(2-trimethylsilanyl-ethoxymethyl)-1H-indol-5-yl]-propionic acid ethyl ester were dissolved in 40 ml dioxane, then treated with 7.6 ml lithium hydroxide solution (1 molar in water) and stirred for 16 hours at ambient temperature. Extraction of the reaction mixture with H2O/HCl and dichloromethane, followed by drying of the organic phase with sodium sulfate and evaporation, gave 1.27 g crude product, which was purified by chromatography (silicagel, eluent: gradient of n-heptane/EtOAc) yield to 0.98 g rac-2-propoxy-3-[1-(2-trimethylsilanyl-ethoxymethyl)-1H-indol-5-yl]-propionic acid as a light yellow oil.

Workup

  1. extractionExtraction of the reaction mixture with H2O/HCl and dichloromethane
  2. dry with materialby drying of the organic phase with sodium sulfate and evaporation
  3. customgave 1.27 g crude product, which
  4. customwas purified by chromatography (silicagel, eluent: gradient of n-heptane/EtOAc)

Sources & evidence

ORD record
ord-794248167bb848c19b3e5f634b421e89
Source dataset
uspto-grants-2005_05
Patent number
US06890947B2

Reaction notes

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