Imidazole → [(6-Bromonaphthalen-2-yl)oxy](tert-butyl)dimethylsilane

HRID 259790

反応式

HRID 259790 の反応式
[Br:1][C:2]1[CH:3]=[C:4]2[C:9](=[CH:10][CH:11]=1)[CH:8]=[C:7]([OH:12])[CH:6]=[CH:5]2.N1C=CN=C1.[Si:18](Cl)([C:21]([CH3:24])([CH3:23])[CH3:22])([CH3:20])[CH3:19].[SiH3]Cl>CN(C=O)C>[Br:1][C:2]1[CH:3]=[C:4]2[C:9](=[CH:10][CH:11]=1)[CH:8]=[C:7]([O:12][Si:18]([C:21]([CH3:24])([CH3:23])[CH3:22])([CH3:20])[CH3:19])[CH:6]=[CH:5]2

参加物

6

反応物 4

HCID 795Imidazole2 回HCID 271446-Bromo-2-naphthalenolHCID 28928tert-Butyldimethylsilyl chlorideHCID 61622Chlorosilane

生成物 1

HCID 13473083[(6-Bromonaphthalen-2-yl)oxy](tert-butyl)dimethylsilane収率 74.1%

試薬・触媒・溶媒 1

HCID 6228Dimethylformamide溶媒

実験手順

6-Bromo-2-naphthol (10 g, 44 mmol), imidazole (7.4 g, 110 mmol), and t-butyldimethylsilyl chloride (10 g, 66 mmol) were stirred in DMF (50 mL) at room temperature overnight. TLC analysis indicated incomplete reaction, so additional imidazole (0.6 g) and silyl chloride (1.3 g) were added, and stirring continued 1 day. After evaporation of DMF, the mixture was extracted with EtOAc and 5% aqueous KHSO4, dried (Na2SO4), and evaporated. The crude product was purified by silica gel chromatography, eluting with hexane, to yield a colorless solid (11 g). mp 62°-63° C. 1H NMR (300 MHz, CDCl3): 7.90 (d, 1H, J=l Hz), 7.62 (d, 1H, J=9 Hz), 7.55 (d, 1H, J=9 Hz), 7.46 (dd, 1H, J=9, 2 Hz), 7.14 (d, 1H, J=2 Hz), 7.08 (dd, 1H, J=9,2 Hz), 1.00 (s, 9H), 0.23 (s, 6H). MS(CH4): 365 (20%, M+C2H5, 1 Br isotope pattern), 337 (base, M+H, 1 Br isotope pattern).

後処理

  1. customreaction
  2. customAfter evaporation of DMF
  3. extractionthe mixture was extracted with EtOAc and 5% aqueous KHSO4
  4. dry with materialdried (Na2SO4)
  5. customevaporated
  6. customThe crude product was purified by silica gel chromatography
  7. washeluting with hexane

出典と根拠

ORDレコード
ord-a5d80d7583b246718f86a6891c700862
出典データセット
uspto-grants-1996_06
特許番号
US05523302

関連ノート

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