Dimethylformamide → 1-Methyl-4-phenyl-1H-1,2,3-triazole-5-carbaldehyde

HRID 402342ノート

反応式

HRID 402342 の反応式
[CH3:1][N:2]1[CH:6]=[C:5]([C:7]2[CH:12]=[CH:11][CH:10]=[CH:9][CH:8]=2)[N:4]=[N:3]1.[Li]CCCC.CN([CH:21]=[O:22])C.[Cl-].[NH4+]>C1COCC1>[CH3:1][N:2]1[C:6]([CH:21]=[O:22])=[C:5]([C:7]2[CH:8]=[CH:9][CH:10]=[CH:11][CH:12]=2)[N:4]=[N:3]1

参加物

6

反応物 4

HCID 6228DimethylformamideHCID 25517Ammonium ChlorideHCID 1130966315965-36-3HCID 178418339Butyllithium

生成物 1

HCID 735550571-Methyl-4-phenyl-1H-1,2,3-triazole-5-carbaldehyde収率 68%

試薬・触媒・溶媒 1

HCID 8028Tetrahydrofuran溶媒

反応条件

温度
-75 °C

実験手順

To a solution of 1-methyl-4-phenyl-1H-[1,2,3]triazole (165 mg, 1.04 mmol) in THF (5.2 mL) was added n-BuLi (1.6 M in hexane, 777 μL, 1.24 mmol) dropwise at −75° C. under Argon. The resulted orange solution was stirred at −75° C. for 40 min, then DMF (104 μL, 1.35 mmol) was added dropwise at −75° C. and the reaction mixture was allowed to warm up to room temperature over 1 h. The mixture was then poured into saturated ammonium chloride solution and extracted with ethyl acetate and the combined organic extracts washed with brine, dried over sodium sulphate, filtered and evaporated. Purification by chromatography (silica, 0 to 50% ethyl acetate in heptane) afforded the title compound (131 mg, 68%) as a white solid. MS: m/e=187.0 [M]+.

後処理

  1. temperatureto warm up to room temperature over 1 h
  2. extractionextracted with ethyl acetate
  3. washthe combined organic extracts washed with brine
  4. dry with materialdried over sodium sulphate
  5. filtrationfiltered
  6. customevaporated
  7. customPurification by chromatography (silica, 0 to 50% ethyl acetate in heptane)

出典と根拠

ORDレコード
ord-ee94013090da459791dcd4df31f4e82a
出典データセット
uspto-grants-2014_06
特許番号
US08742097B2

反応ノート

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