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Dimethyl Sulfoxide → 3-[3,4-Dichloro-5-({[(1,1-dimethylethyl)(dimethyl)silyl]oxy}methyl)phenyl]propanenitrile

HRID 337588
ノート
印刷プレビュー

反応式

HRID 337588 の反応式
CS(C)=O.CS(O[CH2:10][CH2:11][C:12]1[CH:17]=[C:16]([CH2:18][O:19][Si:20]([C:23]([CH3:26])([CH3:25])[CH3:24])([CH3:22])[CH3:21])[C:15]([Cl:27])=[C:14]([Cl:28])[CH:13]=1)(=O)=O.[C-:29]#[N:30].[K+]>CCOCC>[Cl:28][C:14]1[CH:13]=[C:12]([CH2:11][CH2:10][C:29]#[N:30])[CH:17]=[C:16]([CH2:18][O:19][Si:20]([C:23]([CH3:26])([CH3:25])[CH3:24])([CH3:22])[CH3:21])[C:15]=1[Cl:27]
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

5

反応物 3

HCID 679Dimethyl SulfoxideHCID 9032Potassium CyanideHCID 866516682-[3,4-Dichloro-5-({[(1,1-dimethylethyl)(dimethyl)silyl]oxy}methyl)phenyl]ethyl methanesulfonate

生成物 1

HCID 668961283-[3,4-Dichloro-5-({[(1,1-dimethylethyl)(dimethyl)silyl]oxy}methyl)phenyl]propanenitrile

試薬・触媒・溶媒 1

HCID 3283Diethyl Ether溶媒

反応条件

温度
80 °C

実験手順

To a DMSO (0.4 M) solution of 2-[3,4-dichloro-5-({[(1,1-dimethylethyl)(dimethyl)silyl]oxy}methyl)phenyl]ethyl methanesulfonate (1 eq.) from the previous step was added potassium cyanide (1.3 eq.). The resulting solution was stirred at 80° C. for 4 h. The reaction was then diluted with ether and quenched with water. The aqueous layer was separated and back-extracted with ether. The combined organic extracts were washed further with water and brine, dried over Na2SO4, filtered and the filtrate concentrated in vacuo to give the title compound as a pink oil.

後処理

  1. customquenched with water
  2. customThe aqueous layer was separated
  3. extractionback-extracted with ether
  4. washThe combined organic extracts were washed further with water and brine
  5. dry with materialdried over Na2SO4
  6. filtrationfiltered
  7. concentrationthe filtrate concentrated in vacuo

出典と根拠

ORDレコード
ord-2f3969eacae24e35b5c68cc8f3c80755
出典データセット
uspto-grants-2014_11
DOI
10.6084/m9.figshare.5104873.v1
特許番号
US08889714B2

反応ノート

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