Imidazole → (5)-[1-(2-Bromo-phenyl)-ethoxy]-tert-butyl-dimethyl-silane

HRID 1592717

反応式

HRID 1592717 の反応式
[Br:1][C:2]1[CH:10]=[CH:9][CH:8]=[CH:7][C:3]=1[C@@H:4]([OH:6])[CH3:5].[Si:11](Cl)([C:14]([CH3:17])([CH3:16])[CH3:15])([CH3:13])[CH3:12].N1C=CN=C1>>[Br:1][C:2]1[CH:10]=[CH:9][CH:8]=[CH:7][C:3]=1[C@@H:4]([O:6][Si:11]([C:14]([CH3:17])([CH3:16])[CH3:15])([CH3:13])[CH3:12])[CH3:5]

参加物

4

反応物 3

HCID 795ImidazoleHCID 28928tert-Butyldimethylsilyl chlorideHCID 69503311-(2-Bromophenyl)ethan-1-ol

生成物 1

HCID 125465295(5)-[1-(2-Bromo-phenyl)-ethoxy]-tert-butyl-dimethyl-silane収率 82%

実験手順

To a 25 mL flask containing (S)-(−)-2-bromo-alpha-methylbenzyl alcohol (200 mg, 1.0 mmol), tert-butyldimethylsilyl chloride (165 mg, 1.1 mmol), and imidazole (203 mg, 3.0 mmol) flushed with nitrogen was added 5 mL of dimethylformamide. After stirring overnight, the mixture was quenched with saturated sodium bicarbonate, diluted with ethyl acetate, washed with NaH2PO4, saturated aqueous sodium bicarbonate, water, brine, dried (Na2SO4), filtered, and concentrated. Purification by flash chromatography (10 g SiO2, linear gradient 0-10% ethyl acetate/Hexanes, 30 mL/minute, over 30 minutes) gave about 260 mg (0.82 mmol, 82%) of (5)-[1-(2-Bromo-phenyl)-ethoxy]-tert-butyl-dimethyl-silane as a colorless oil. GC/MS (EI): 315 (M). The (5)-[1-(2-Bromo-phenyl)-ethoxy]-tert-butyl-dimethyl-silane was coupled to piperazine in a manner similar to Preparation 1A. LRMS (ESI+): 321.5 (M+1)

後処理

  1. customflushed with nitrogen
  2. additionwas added 5 mL of dimethylformamide
  3. customthe mixture was quenched with saturated sodium bicarbonate
  4. additiondiluted with ethyl acetate
  5. washwashed with NaH2PO4, saturated aqueous sodium bicarbonate, water, brine
  6. dry with materialdried (Na2SO4)
  7. filtrationfiltered
  8. concentrationconcentrated
  9. customPurification by flash chromatography (10 g SiO2, linear gradient 0-10% ethyl acetate/Hexanes, 30 mL/minute, over 30 minutes)

出典と根拠

ORDレコード
ord-68095268d655410ea896a566a67e6eeb
出典データセット
uspto-grants-2007_11
特許番号
US07291619B2

関連ノート

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