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Sodium Iodide → Tert-butyl[2-chloro-1-(iodomethyl)ethoxy]dimethylsilane

HRID 1398133
ノート
印刷プレビュー

反応式

HRID 1398133 の反応式
CC1C=CC(S(O[CH2:12][CH:13]([O:16][Si:17]([C:20]([CH3:23])([CH3:22])[CH3:21])([CH3:19])[CH3:18])[CH2:14][Cl:15])(=O)=O)=CC=1.[I-:24].[Na+]>CC(C)=O>[C:20]([Si:17]([O:16][CH:13]([CH2:12][I:24])[CH2:14][Cl:15])([CH3:19])[CH3:18])([CH3:23])([CH3:22])[CH3:21]
参加物反応条件実験手順後処理出典と根拠反応ノート

参加物

4

反応物 2

HCID 5238Sodium IodideHCID 866629712-{[Tert-butyl(dimethyl)silyl]oxy}-3-chloropropyl 4-methylbenzenesulfonate

生成物 1

HCID 86662972Tert-butyl[2-chloro-1-(iodomethyl)ethoxy]dimethylsilane収率 74.7%

試薬・触媒・溶媒 1

HCID 180Acetone溶媒

反応条件

温度
80 °C

実験手順

To a mixture of 2-{[tert-butyl(dimethyl)silyl]oxy}-3-chloropropyl 4-methylbenzenesulfonate (20.3 g) in acetone (200 mL) was added sodium iodide (19.7 g), and the mixture was stirred at 80° C. for 3 hr. The reaction mixture was concentrated, water was added to the residue, and the mixture was extracted with hexane. The extract was dried over anhydrous magnesium sulfate, and the solvent was evaporated under reduced pressure. The residue was purified by silica gel column chromatography (ethyl acetate/hexane) to give the title compound (13.4 g).

後処理

  1. concentrationThe reaction mixture was concentrated
  2. additionwater was added to the residue
  3. extractionthe mixture was extracted with hexane
  4. dry with materialThe extract was dried over anhydrous magnesium sulfate
  5. customthe solvent was evaporated under reduced pressure
  6. customThe residue was purified by silica gel column chromatography (ethyl acetate/hexane)

出典と根拠

ORDレコード
ord-139e8e51496a4863ac683f140d3771c7
出典データセット
uspto-grants-2014_12
DOI
10.6084/m9.figshare.5104873.v1
特許番号
US08901309B2

反応ノート

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