Cyclopropylacetylene → HCID 86702007、化合物

HRID 717979ノート

反応式

HRID 717979 の反応式
Cl[C:2]([C:4]1[S:8][C:7]([C:9]([O:11][CH3:12])=[O:10])=[CH:6][CH:5]=1)=[O:3].[C:13]([CH:15]1[CH2:17][CH2:16]1)#[CH:14]>C(N(CC)CC)C.CO.[Cu]I>[CH:15]1([C:13]#[C:14][C:2]([C:4]2[S:8][C:7]([C:9]([O:11][CH3:12])=[O:10])=[CH:6][CH:5]=2)=[O:3])[CH2:17][CH2:16]1

参加物

6

反応物 2

HCID 138823CyclopropylacetyleneHCID 21779986Methyl 5-(chlorocarbonyl)thiophene-2-carboxylate

生成物 1

HCID 86702007HCID 86702007、化合物

試薬・触媒・溶媒 3

HCID 24350Copper(1+) iodide; Copper(I) iodide; Cuprous iodide; Cuprous iodide (CuI)触媒HCID 887Methanol溶媒HCID 8471Triethylamine溶媒

実験手順

Methyl 5-(chlorocarbonyl)thiophene-2-carboxylate (500 mg, 2.443 mmol) was dissolved in triethylamine (5 mL) and the suspension was degassed with nitrogen. Copper(I) iodide (40 mg, 0.210 mmol) and bistriphenylphosphine palladium (II) chloride (40 mg, 0.057 mmol) were added followed by ethynylcyclopropane (162 mg, 2.443 mmol). The mixture was stirred overnight, diluted with methanol and concentrated to dryness. The crude material was partitioned between dichloromethane and water. The organic extracts were dried with sodium sulfate, filtered, concentrated and purified by normal phase chromatography to afford the title compound.

後処理

  1. customthe suspension was degassed with nitrogen
  2. concentrationconcentrated to dryness
  3. customThe crude material was partitioned between dichloromethane and water
  4. dry with materialThe organic extracts were dried with sodium sulfate
  5. filtrationfiltered
  6. concentrationconcentrated
  7. custompurified by normal phase chromatography

出典と根拠

ORDレコード
ord-cbf5339cbc8242349c835f8003b0290c
出典データセット
uspto-grants-2015_11
特許番号
US09193723B2

反応ノート

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