3-(1-Azidotridecyl)-5-trimethylsilylfuran → 3-(1-Aminotridecyl)-5-trimethylsilylfuran

HRID 488214ノート

反応式

HRID 488214 の反応式
[H-].[Al+3].[Li+].[H-].[H-].[H-].[N:7]([CH:10]([C:23]1[CH:27]=[C:26]([Si:28]([CH3:31])([CH3:30])[CH3:29])[O:25][CH:24]=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-]>O1CCCC1>[NH2:7][CH:10]([C:23]1[CH:27]=[C:26]([Si:28]([CH3:31])([CH3:30])[CH3:29])[O:25][CH:24]=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]

参加物

4

反応物 2

HCID 190198473-(1-Azidotridecyl)-5-trimethylsilylfuranHCID 21226445Aluminium lithium hydride

生成物 1

HCID 150370773-(1-Aminotridecyl)-5-trimethylsilylfuran

試薬・触媒・溶媒 1

HCID 8028Tetrahydrofuran溶媒2 回

実験手順

Lithium aluminum hydride (a 1M solution in tetrahydrofuran; 1.1 ml, 1.1 mmol) was added dropwise to a solution of 3-(1-azidotridecyl)-5-trimethylsilylfuran (334 mg, 0.92 mmol) in tetrahydrofuran at room temperature. After one hour at room temperature, the excess hydride was destroyed by adding acetone slowly to the mixture with cooling. Sodium sulfate (ca. 0.5 g) was added 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 containing 0.2% triethylamine. Fractions with Rf of about 0.18 on evaporation gave the title amine as a pale yellow oil.

後処理

  1. customthe excess hydride was destroyed
  2. additionby adding acetone slowly to the mixture
  3. temperaturewith cooling
  4. additionSodium sulfate (ca. 0.5 g) was added
  5. extractionthe mixture was extracted thoroughly with ethyl acetate
  6. customEvaporation of the
  7. dry with materialdried (magnesium sulfate)
  8. customextracts gave an oil, which
  9. customwas purified by flash chromatography on silica using 5% methanol/dichloromethane containing 0.2% triethylamine
  10. customFractions with Rf of about 0.18 on evaporation

出典と根拠

ORDレコード
ord-e5e84b24cc6f4795b20e7cb4e14446e1
出典データセット
uspto-grants-1994_03
特許番号
US05298633

反応ノート

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