4-(1-Azidotridecyl)-2-triethylsilylfuran → 4-(1-Aminotridecyl)-2-triethylsilylfuran

HRID 273966Notes

Reaction equation

HRID 273966 reaction equation
[H-].[Al+3].[Li+].[H-].[H-].[H-].[N:7]([CH:10]([C:23]1[CH:24]=[C:25]([Si:28]([CH2:33][CH3:34])([CH2:31][CH3:32])[CH2:29][CH3:30])[O:26][CH:27]=1)[CH2:11][CH2:12][CH2:13][CH2:14][CH2:15][CH2:16][CH2:17][CH2:18][CH2:19][CH2:20][CH2:21][CH3:22])=[N+]=[N-]>C1COCC1>[NH2:7][CH:10]([C:23]1[CH:24]=[C:25]([Si:28]([CH2:33][CH3:34])([CH2:31][CH3:32])[CH2:29][CH3:30])[O:26][CH:27]=1)[CH2:11][CH2:12][CH2:13][CH2:14][CH2:15][CH2:16][CH2:17][CH2:18][CH2:19][CH2:20][CH2:21][CH3:22]

Participants

4

Reactant 2

HCID 194331464-(1-Azidotridecyl)-2-triethylsilylfuranHCID 21226445Aluminium lithium hydride

Product 1

HCID 150370864-(1-Aminotridecyl)-2-triethylsilylfuran

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

A solution of lithium aluminum hydride (a 1.0M solution in THF; 4.22 ml, 4.22 mmol) was added slowly to a solution of 4-(1-azidotridecyl)-2-triethylsilylfuran (1.55 g, 3.84 mmol) at 0 degrees C. under argon. After stirring at room temperature for 2 hours, the mixture was cooled to 0 degrees C. and quenched with 2M sodium hydroxide. Anhydrous sodium sulfate was added to coagulate the aluminum salt and the mixture was extracted thoroughly with ethyl acetate. Evaporation of the dried (magnesium sulfate) extracts gave an oil, which was purified by flash chromatography on silica using 5% methanol/dichloromethane to give the titled amine.

Workup

  1. temperaturethe mixture was cooled to 0 degrees C
  2. customand quenched with 2M sodium hydroxide
  3. additionAnhydrous sodium sulfate was added
  4. extractionthe mixture was extracted thoroughly with ethyl acetate
  5. customEvaporation of the
  6. dry with materialdried (magnesium sulfate)
  7. customextracts gave an oil, which
  8. customwas purified by flash chromatography on silica using 5% methanol/dichloromethane

Sources & evidence

ORD record
ord-98e8e4a1d20d4bb2879ced58952c1829
Source dataset
uspto-grants-1995_02
Patent number
US05387606

Reaction notes

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