Azidotrimethylsilane → HCID 178419355, 화합물

HRID 385747

반응식

HRID 385747 반응식
[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

참가 물질

6

반응물 3

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

생성물 1

HCID 178419355HCID 178419355, 화합물

시약·촉매·용매 2

HCID 962Water용매4회HCID 6386tert-Butanol용매

반응 조건

온도
100 °C

실험 절차

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.

후처리

  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)

출처 및 근거

ORD 기록
ord-e1d2c4c42db4498d8be0729f57f379c5
출처 데이터셋
uspto-grants-2013_02
특허 번호
US08367706B2

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