Aluminium lithium hydride → (1-((Trimethylsilyl)methyl)-1h-1,2,3-triazol-4-yl)methanol

HRID 1942817

反応式

HRID 1942817 の反応式
[CH3:1][Si:2]([CH2:5][N:6]1[CH:10]=[C:9]([C:11](OCC)=[O:12])[N:8]=[N:7]1)([CH3:4])[CH3:3].[H-].[H-].[H-].[H-].[Li+].[Al+3]>C1COCC1>[CH3:4][Si:2]([CH2:5][N:6]1[CH:10]=[C:9]([CH2:11][OH:12])[N:8]=[N:7]1)([CH3:1])[CH3:3]

参加物

4

反応物 2

HCID 21226445Aluminium lithium hydrideHCID 59627360ethyl 1-[(trimethylsilyl)methyl]-1H-1,2,3-triazole-4-carboxylate

生成物 1

HCID 59627317(1-((Trimethylsilyl)methyl)-1h-1,2,3-triazol-4-yl)methanol

試薬・触媒・溶媒 1

HCID 8028Tetrahydrofuran溶媒

反応条件

温度
0 °C

実験手順

A solution of ethyl 1-[(trimethylsilyl)methyl]-1H-1,2,3-triazole-4-carboxylate (1.00 g, 4.40 mmol) and THF (14.6 mL) was cooled to 0° C. and a solution of LAH (4.40 mL, 1M in THF) was added dropwise. The mixture was stirred for 1 h, and the cold bath was removed and stirred for an additional hour. The reaction was cooled to 0° C. and a solution of saturated sodium sulfate (4.4 mL) was added. The mixture was warmed to room temperature, stirred 30 min, and filtered. The filtrate was concentrated and the residue azeotroped with ethanol to afford a colorless oil purified via MPLC, 40M column, 1-8% MeOH in DCM afforded the title material as a clear, colorless oil. MS: cal'd 186 (MH+), exp 186 (MH+).

後処理

  1. customthe cold bath was removed
  2. stirringstirred for an additional hour
  3. additiona solution of saturated sodium sulfate (4.4 mL) was added
  4. temperatureThe mixture was warmed to room temperature
  5. stirringstirred 30 min
  6. filtrationfiltered
  7. concentrationThe filtrate was concentrated
  8. customthe residue azeotroped with ethanol
  9. customto afford a colorless oil
  10. custompurified via MPLC, 40M column, 1-8% MeOH in DCM

出典と根拠

ORDレコード
ord-4b7fa1927d4b497b87da9d24283d714c
出典データセット
uspto-grants-2013_03
特許番号
US08389553B2

関連ノート

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