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N-Iodosuccinimide → tert-Butyl-[4-iodo-1-(Propylcyclobutyl)but-3-enyloxy]dimethylsilane

HRID 2080905
ノート
印刷プレビュー

反応式

HRID 2080905 の反応式
[C:1]([Si:5]([CH3:19])([CH3:18])[O:6][CH:7]([C:11]1([CH2:15][CH2:16][CH3:17])[CH2:14][CH2:13][CH2:12]1)[CH2:8][C:9]#[CH:10])([CH3:4])([CH3:3])[CH3:2].[I:20]N1C(=O)CCC1=O>C(Cl)Cl.[H-].[Cl-].C1([Zr+2]C2C=CC=C2)C=CC=C1>[C:1]([Si:5]([O:6][CH:7]([C:11]1([CH2:15][CH2:16][CH3:17])[CH2:14][CH2:13][CH2:12]1)[CH2:8][CH:9]=[CH:10][I:20])([CH3:19])[CH3:18])([CH3:3])([CH3:4])[CH3:2]
参加物実験手順後処理出典と根拠反応ノート

参加物

5

反応物 2

HCID 120273N-IodosuccinimideHCID 15475299tert-Butyldimethyl-[1-(1-propylcyclobutyl)but-3-ynyloxy]silane

生成物 1

HCID 53961856tert-Butyl-[4-iodo-1-(Propylcyclobutyl)but-3-enyloxy]dimethylsilane収率 74.6%

試薬・触媒・溶媒 2

HCID 178420592HCID 178420592、化合物触媒HCID 6344Dichloromethane溶媒

実験手順

Bis(cyclopentadienyl)zirconiumchloride hydride (3.1 g, 12.0 mmol) was added to a solution of alkyne 5 (1.7 g, 3.94 mmol) in CH2Cl2 (20 mL) at 23° C. After 0.5 h N-iodosuccinimide (2.6 g, 12.0 mmol) was added. The reaction was stirred for 0.5 h, concentrated in vacuo and the residue was diluted with pentane and washed with saturated aqueous sodium bisulfite. The organic portion was dried (Na2SO4), filtered and concentrated in vacuo. Purification of the residue by FCC (silica gel, 100% pentane) gave 1.2 g (71%) of the vinyl iodide 6 as a clear, light yellow oil.

後処理

  1. concentrationconcentrated in vacuo
  2. additionthe residue was diluted with pentane
  3. washwashed with saturated aqueous sodium bisulfite
  4. dry with materialThe organic portion was dried (Na2SO4)
  5. filtrationfiltered
  6. concentrationconcentrated in vacuo
  7. customPurification of the residue by FCC (silica gel, 100% pentane)

出典と根拠

ORDレコード
ord-777fd2a74bc14e219d1f6b218f2fc478
出典データセット
uspto-grants-2011_04
DOI
10.6084/m9.figshare.5104873.v1
特許番号
US07932420B2

反応ノート

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