Imidazole → 2-[2-[[Dimethyl(1,1,2-trimethylpropyl)silyl]oxy]ethyl]benzene bromide

HRID 465868

反応式

HRID 465868 の反応式
[Br:1][C:2]1[CH:10]=[CH:9][CH:8]=[CH:7][C:3]=1[CH2:4][CH2:5][OH:6].N1C=CN=C1.[CH3:16][Si:17](Cl)([CH3:24])[C:18]([CH:21]([CH3:23])[CH3:22])([CH3:20])[CH3:19]>C(Cl)Cl.O.CCOCC>[Br-:1].[CH3:16][Si:17]([CH3:24])([C:18]([CH3:20])([CH3:19])[CH:21]([CH3:23])[CH3:22])[O:6][CH2:5][CH2:4][C:3]1[CH:7]=[CH:8][CH:9]=[CH:10][CH:2]=1

参加物

7

反応物 3

HCID 795ImidazoleHCID 144239Dimethylthexylsilyl chlorideHCID 27340892-(2-Bromophenyl)ethan-1-ol

生成物 1

HCID 198753762-[2-[[Dimethyl(1,1,2-trimethylpropyl)silyl]oxy]ethyl]benzene bromide

試薬・触媒・溶媒 3

HCID 962Water溶媒HCID 3283Diethyl Ether溶媒HCID 6344Dichloromethane溶媒

反応条件

温度
0 °C

実験手順

2-Bromophenethyl alcohol (43.80 g, 217.9 mmol) was dissolved in anhydrous CH2Cl2 (200 mL) and imidazole (16.32 g, 239.6 mmol) was added and stirred under argon 0° C. Dimethylthexylsilyl chloride (42.83 g, 239.6 mmol) was added dropwise and the reaction mixture was stirred for three days at room temperature. It was diluted with H2O (50 mL) and ether (100 mL) and partitioned. The aqueous layer was extracted with ether (2×100 mL). The combined organic layers were washed with 5% aqueous HCl (1 time), H2O (1 time), aqueous NaHCO3 (1 time), H2O (1 time), and brine, then dried (MgSO4) and concentrated in vacuo to obtain a yellow oil. The crude product was Kugelrohr distilled (55°-80° ) under oil pump vacuum to give the purified title compound.

後処理

  1. stirringthe reaction mixture was stirred for three days at room temperature
  2. custompartitioned
  3. extractionThe aqueous layer was extracted with ether (2×100 mL)
  4. washThe combined organic layers were washed with 5% aqueous HCl (1 time), H2O (1 time), aqueous NaHCO3 (1 time), H2O (1 time), and brine
  5. dry with materialdried (MgSO4)
  6. concentrationconcentrated in vacuo
  7. customto obtain a yellow oil
  8. distillationdistilled (55°-80° ) under oil pump vacuum
  9. customto give the
  10. custompurified title compound

出典と根拠

ORDレコード
ord-a0c538e554cc4726895b1e987c7f877d
出典データセット
uspto-grants-1992_10
特許番号
US05153327

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