Hydrochloric Acid → 1-(2-Trimethylsilylethyl)oxymethylindole-5-carboxaldehyde

HRID 2181188Notes

Reaction equation

HRID 2181188 reaction equation
[H-].[Na+].[NH:3]1[C:11]2[C:6](=[CH:7][C:8]([CH:12]=[O:13])=[CH:9][CH:10]=2)[CH:5]=[CH:4]1.[CH3:14][Si:15]([CH3:22])([CH3:21])[CH2:16][CH2:17][O:18][CH2:19]Cl.Cl>CN(C)C=O>[CH3:14][Si:15]([CH3:22])([CH3:21])[CH2:16][CH2:17][O:18][CH2:19][N:3]1[C:11]2[C:6](=[CH:7][C:8]([CH:12]=[O:13])=[CH:9][CH:10]=2)[CH:5]=[CH:4]1

Participants

6

Reactant 4

HCID 313Hydrochloric AcidHCID 24758Sodium hydrideHCID 589040Indole-5-carboxaldehydeHCID 27242712-Chloromethyl 2-(trimethylsilyl)ethyl ether

Product 1

HCID 224856951-(2-Trimethylsilylethyl)oxymethylindole-5-carboxaldehyde

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent2×

Procedure

To a stirred suspension of 5.45, sodium hydride (55%) in mineral oil) in 100 ml N,N-dimethylformamide was added at 0-5° C. a solution of 16.8 g indole-5-carboxaldehyde in 100 ml N,N-dimethylformamide followed by 24.46 ml of 2-(trimethylsilyl)-ethoxymethyl chloride. The reaction mixture was then warmed up to ambient temperature and stirring continued for 16 hours. It was then poured onto ice, neutralized to pH 4 with HCl (1N) and extracted 3 times with ethyl acetate. The combined organic phases were washed with water, dried over magnesium sulfate and evaporated to give a brown oil, which was purified by chromatography (silicagel, eluent: gradient of n-heptane/EtOAc) to yield 25.52 g 1-(2-trimethylsilanyl-ethoxymethyl)-1H-indole-5-carbaldehyde as light yellow oil.

Workup

  1. additionIt was then poured onto ice
  2. extractionextracted 3 times with ethyl acetate
  3. washThe combined organic phases were washed with water
  4. dry with materialdried over magnesium sulfate
  5. customevaporated
  6. customto give a brown oil, which
  7. customwas purified by chromatography (silicagel, eluent: gradient of n-heptane/EtOAc)

Sources & evidence

ORD record
ord-db4d87f421194eb49dc80b15ea3f7ce3
Source dataset
uspto-grants-2005_05
Patent number
US06890947B2

Reaction notes

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