Dimethylformamide → 4-(2-Fluorophenyl)-1-methyl-1H-1,2,3-triazole-5-carbaldehyde

HRID 402364ノート

反応式

HRID 402364 の反応式
[F:1][C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][C:3]=1[C:8]1[N:9]=[N:10][N:11]([CH3:13])[CH:12]=1.[Li]CCCC.CN([CH:22]=[O:23])C.[Cl-].[NH4+]>C1COCC1>[F:1][C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][C:3]=1[C:8]1[N:9]=[N:10][N:11]([CH3:13])[C:12]=1[CH:22]=[O:23]

参加物

6

反応物 4

HCID 6228DimethylformamideHCID 25517Ammonium ChlorideHCID 674985534-(2-fluorophenyl)-1-methyl-1H-1,2,3-triazoleHCID 178418339Butyllithium

生成物 1

HCID 866647624-(2-Fluorophenyl)-1-methyl-1H-1,2,3-triazole-5-carbaldehyde収率 87.2%

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 4-(2-fluorophenyl)-1-methyl-1H-1,2,3-triazole (1.44 g, 8.1 mmol) in THF (41 mL) was added n-BuLi (1.6 M in hexane, 6.10 mL, 9.8 mmol) dropwise at −75° C. under Argon. The resulted orange solution was stirred at −75° C. for 1 h, then DMF (0.82 mL, 10.6 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 (1.45 g, 87%) as an off white solid. MS: m/e=206.0 [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-3755f18473d943d6acb6c400b490b90d
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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