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

HRID 390769노트

반응식

HRID 390769 반응식
[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]

참가 물질

7

반응물 3

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

생성물 1

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

시약·촉매·용매 3

HCID 24350Copper(1+) iodide; Copper(I) iodide; Cuprous iodide; Cuprous iodide (CuI)촉매HCID 178418476HCID 178418476, 화합물촉매HCID 6228Dimethylformamide용매

실험 절차

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.

후처리

  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

출처 및 근거

ORD 기록
ord-47a109eae293408b818b08e6b8721a45
출처 데이터셋
uspto-grants-2013_02
특허 번호
US08383659B2

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