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Trimethylsilylacetylene → 2-(5-trimethylsilylethynyl-3-pyridyloxy)-N-(4-methylpent-2-yn-4-yl)butyramide

HRID 1374920
ノート
印刷プレビュー

反応式

HRID 1374920 の反応式
Br[C:2]1[CH:3]=[C:4]([O:8][CH:9]([CH2:19][CH3:20])[C:10]([NH:12][C:13]([CH3:18])([CH3:17])[C:14]#[C:15][CH3:16])=[O:11])[CH:5]=[N:6][CH:7]=1.[CH3:21][Si:22]([C:25]#[CH:26])([CH3:24])[CH3:23]>C(N(CC)CC)C.C(OCC)C.[Cu]Cl>[CH3:21][Si:22]([C:25]#[C:26][C:2]1[CH:3]=[C:4]([O:8][CH:9]([CH2:19][CH3:20])[C:10]([NH:12][C:13]([CH3:18])([CH3:17])[C:14]#[C:15][CH3:16])=[O:11])[CH:5]=[N:6][CH:7]=1)([CH3:24])[CH3:23]
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

6

反応物 2

HCID 66111Trimethylsilylacetylene2 回HCID 21078374HCID 21078374、化合物

生成物 1

HCID 210784012-(5-trimethylsilylethynyl-3-pyridyloxy)-N-(4-methylpent-2-yn-4-yl)butyramide

試薬・触媒・溶媒 3

HCID 62652Cuprous chloride触媒HCID 3283Diethyl Ether溶媒HCID 8471
Triethylamine
溶媒

反応条件

温度
90 °C

実験手順

2-(5-Bromo-3-pyridyloxy)-N-(4-methylpent-2-yn-4-yl)butyramide (0.40 g), trimethylsilylacetylene (0.24 ml), copper (I) chloride (0.015 g) and palladium dichloride bis(triphenyl)phosphine (0.030 g) in dry triethylamine (4 ml) were sealed in a glass tube and heated to 90° C. for 3 hours. The mixture was cooled to ambient temperature and stored for 18 hours. Further trimethylsilylacetylene (0.24 ml) and palladium dichloride bis(triphenyl)-phosphine (0.030 g) were added and the mixture re-heated in the sealed tube for another 5.5 hours. The reaction mixture was cooled to ambient temperature, stored for 72 hours, diluted with diethyl ether and washed with water (three times). The organic phase was separated, dried over magnesium sulphate and evaporated under reduced pressure to give a dark yellow gum, ca. 0.4 g, containing the required product, which was used in the next Stage without further purification.

後処理

  1. temperatureThe mixture was cooled to ambient temperature
  2. temperaturethe mixture re-heated in the sealed tube for another 5.5 hours
  3. temperatureThe reaction mixture was cooled to ambient temperature
  4. waitstored for 72 hours
  5. washwashed with water (three times)
  6. customThe organic phase was separated
  7. dry with materialdried over magnesium sulphate
  8. customevaporated under reduced pressure
  9. customto give a dark yellow gum, ca. 0.4 g

出典と根拠

ORDレコード
ord-40abed4075dd486d9538de71bf5d5e8f
出典データセット
uspto-grants-2007_01
DOI
10.6084/m9.figshare.5104873.v1
特許番号
US07166621B2

反応ノート

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このページの内容参加物反応条件実験手順後処理出典と根拠反応ノート