Cyclopentylacetylene → Methyl 4-(cyclopentylethynyl)-2-methylbenzoate

HRID 2102918

反応式

HRID 2102918 の反応式
Br[C:2]1[CH:11]=[CH:10][C:5]([C:6]([O:8][CH3:9])=[O:7])=[C:4]([CH3:12])[CH:3]=1.[C:13]([CH:15]1[CH2:19][CH2:18][CH2:17][CH2:16]1)#[CH:14]>C(N(CC)CC)C.[Cu](I)I.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>[CH:15]1([C:13]#[C:14][C:2]2[CH:11]=[CH:10][C:5]([C:6]([O:8][CH3:9])=[O:7])=[C:4]([CH3:12])[CH:3]=2)[CH2:19][CH2:18][CH2:17][CH2:16]1

参加物

6

反応物 2

HCID 136725CyclopentylacetyleneHCID 22031226Methyl 4-bromo-2-methylbenzoate

生成物 1

HCID 57804197Methyl 4-(cyclopentylethynyl)-2-methylbenzoate

試薬・触媒・溶媒 3

HCID 83717Copper iodide触媒HCID 178418476HCID 178418476、化合物触媒HCID 8471Triethylamine溶媒

反応条件

温度
80 °C

実験手順

Methyl 4-bromo-2-methylbenzoate (1.0 g, 4.4 mmol) was dissolved in triethylamine (5 mL). To the mixture was added copper iodide (43 mg, 5 mol %), followed by PdCl2(PPh3)2 (157 mg, 5 mol %) and ethynylcyclopentane (0.75 mL, 5.3 mmol). The mixture was heated in a sealed pressure tube at 80° C. for 3 hours. After completion of the reaction, the triethylamine was evaporated and the residue was dissolved in EtOAc and filtered through Celite®. The organic layer was washed with water, brine, and dried (Na2SO4), then filtered and concentrated under vacuum. The residue was purified by column chromatography on sililca gel using EtOAc-hexane (0-100% gradient) as eluet to give the desired product.

後処理

  1. customAfter completion of the reaction
  2. customthe triethylamine was evaporated
  3. dissolutionthe residue was dissolved in EtOAc
  4. filtrationfiltered through Celite®
  5. washThe organic layer was washed with water, brine
  6. dry with materialdried (Na2SO4)
  7. filtrationfiltered
  8. concentrationconcentrated under vacuum
  9. customThe residue was purified by column chromatography on sililca gel

出典と根拠

ORDレコード
ord-5857646d2e6a4d60b7c85b4128a7d606
出典データセット
uspto-grants-2009_08
特許番号
US07576099B2

関連ノート

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