Azidotrimethylsilane → HCID 178419355、化合物

HRID 385747

反応式

HRID 385747 の反応式
[Br:1][C:2]1[CH:7]=[CH:6][C:5]([C:8]#[CH:9])=[CH:4][CH:3]=1.C[Si]([N:14]=[N+:15]=[N-:16])(C)C.O=C1O[C@H]([C@H](CO)O)C([O-])=C1O.[Na+]>CC(O)(C)C.O>[Br:1][C:2]1[CH:7]=[CH:6][C:5]([C:8]2[N:14]=[N:15][NH:16][CH:9]=2)=[CH:4][CH:3]=1

参加物

6

反応物 3

HCID 78378AzidotrimethylsilaneHCID 136603Benzene, 1-bromo-4-ethynyl-HCID 23667548Sodium Ascorbate

生成物 1

HCID 178419355HCID 178419355、化合物

試薬・触媒・溶媒 2

HCID 962Water溶媒4 回HCID 6386tert-Butanol溶媒

反応条件

温度
100 °C

実験手順

1-Bromo-4-ethynylbenzene (650 mg, 3.59 mmol) and trimethylsilyl azide (3.57 mL, 26.9 mmol) were combined in t-BuOH (5.0 mL) and water (3.0 mL) CuSO4.5H2O (90 mg, 0.36 mmol) in water (1.0 mL) and sodium ascorbate (285 mg, 1.44 mmol) in water (1.0 mL) were added, and the sealed reaction mixture was stirred at 100° C. for 48 h. The mixture was diluted with water and extracted with EtOAc (3×). The combined organic layers were washed with brine, dried (MgSO4), filtered, and evaporated. Flash chromatography (dry load, 0-50% EtOAc/hexanes) afforded the title compound as a colorless solid.

後処理

  1. customthe sealed reaction mixture
  2. extractionextracted with EtOAc (3×)
  3. washThe combined organic layers were washed with brine
  4. dry with materialdried (MgSO4)
  5. filtrationfiltered
  6. customevaporated
  7. dry with materialFlash chromatography (dry load, 0-50% EtOAc/hexanes)

出典と根拠

ORDレコード
ord-e1d2c4c42db4498d8be0729f57f379c5
出典データセット
uspto-grants-2013_02
特許番号
US08367706B2

関連ノート

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