Imidazole → Silane, [(8-bromooctyl)oxy](1,1-dimethylethyl)dimethyl-

HRID 654943ノート

反応式

HRID 654943 の反応式
[Br:1][CH2:2][CH2:3][CH2:4][CH2:5][CH2:6][CH2:7][CH2:8][CH2:9][OH:10].[Si:11](Cl)([C:14]([CH3:17])([CH3:16])[CH3:15])([CH3:13])[CH3:12].N1C=CN=C1>CN(C)C=O>[Br:1][CH2:2][CH2:3][CH2:4][CH2:5][CH2:6][CH2:7][CH2:8][CH2:9][O:10][Si:11]([C:14]([CH3:17])([CH3:16])[CH3:15])([CH3:13])[CH3:12]

参加物

5

反応物 3

HCID 795ImidazoleHCID 28928tert-Butyldimethylsilyl chlorideHCID 1626071-Octanol, 8-bromo-

生成物 1

HCID 10969362Silane, [(8-bromooctyl)oxy](1,1-dimethylethyl)dimethyl-

試薬・触媒・溶媒 1

HCID 6228Dimethylformamide溶媒

実験手順

A solution of 8-bromooctan-1-ol (2.15 g, 10.3 mmol), t-butyldimethylsilyl chloride (1.7 g, 11.3 mmol) and imidazole (1.7 g, 25.0 mmol) in dimethylformamide (4 ml) was stirred at room temperature under argon for 48 hours. The reaction was quenched by the addition of water and extracted with hexane. The organic layer was washed with 5% hydrochloric acid, 5% sodium bicarbonate, water, saturated sodium chloride solution, dried over magnesium sulfate, filtered and concentrated to give a colorless oil. Purification by flash chromatography (silica, 0 to 2% ethyl ether/hexane) gave the desired protected alcohol.

後処理

  1. customThe reaction was quenched by the addition of water
  2. extractionextracted with hexane
  3. washThe organic layer was washed with 5% hydrochloric acid, 5% sodium bicarbonate, water, saturated sodium chloride solution
  4. dry with materialdried over magnesium sulfate
  5. filtrationfiltered
  6. concentrationconcentrated
  7. customto give a colorless oil
  8. customPurification by flash chromatography (silica, 0 to 2% ethyl ether/hexane)
  9. customgave the

出典と根拠

ORDレコード
ord-a663ba6f2ab14cef8f8991d91eea4f7c
出典データセット
uspto-grants-1992_07
特許番号
US05134128

反応ノート

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