Triethylamine → 1-(4-Methyl-5-trimethylsilanylethynyl-thiophen-2-yl)-ethanone

HRID 390769ノート

反応式

HRID 390769 の反応式
[CH3:1][Si:2]([C:5]#[CH:6])([CH3:4])[CH3:3].Br[C:8]1[S:12][C:11]([C:13](=[O:15])[CH3:14])=[CH:10][C:9]=1[CH3:16].C(N(CC)CC)C>CN(C=O)C.Cl[Pd](Cl)([P](C1C=CC=CC=1)(C1C=CC=CC=1)C1C=CC=CC=1)[P](C1C=CC=CC=1)(C1C=CC=CC=1)C1C=CC=CC=1.[Cu]I>[CH3:16][C:9]1[CH:10]=[C:11]([C:13](=[O:15])[CH3:14])[S:12][C:8]=1[C:6]#[C:5][Si:2]([CH3:4])([CH3:3])[CH3:1]

参加物

7

反応物 3

HCID 8471TriethylamineHCID 66111TrimethylsilylacetyleneHCID 454803531-(5-Bromo-4-methylthiophen-2-yl)ethan-1-one

生成物 1

HCID 674301401-(4-Methyl-5-trimethylsilanylethynyl-thiophen-2-yl)-ethanone

試薬・触媒・溶媒 3

HCID 24350Copper(1+) iodide; Copper(I) iodide; Cuprous iodide; Cuprous iodide (CuI)触媒HCID 178418476HCID 178418476、化合物触媒HCID 6228Dimethylformamide溶媒

実験手順

Trimethylsilylacetylene (16 ml) is added to a solution of 1-(5-bromo-4-methyl-thiophen-2-yl)-ethanone (16.9 q, example 1, step A), Pd(PPh3)2Cl2 (3.78 g), CuI (1.46 g) and triethylamine (16 ml) in DMF (15 ml). After 3 hours at room temperature, the reaction is quenched with water and extracted three times with ethyl acetate. The organic phases are combined, dried over Na2SO4 and concentrated in vacuo. The crude product is purified by filtration over a plug of silica gel eluting with dichloromethane to yield 1-(4-methyl-5-trimethylsilanylethynyl-thiophen-2-yl)-ethanone (18.2 g) as yellow solid. The compound is used without further purification.

後処理

  1. customthe reaction is quenched with water
  2. extractionextracted three times with ethyl acetate
  3. dry with materialdried over Na2SO4
  4. concentrationconcentrated in vacuo
  5. filtrationThe crude product is purified by filtration over a plug of silica gel eluting with dichloromethane

出典と根拠

ORDレコード
ord-47a109eae293408b818b08e6b8721a45
出典データセット
uspto-grants-2013_02
特許番号
US08383659B2

反応ノート

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