Tetrahydrofuran → 1,4-Diethynylbenzene

HRID 556136

反応式

HRID 556136 の反応式
I[C:2]1[CH:7]=[CH:6][C:5](I)=[CH:4][CH:3]=1.[CH2:9]1[CH2:13]OCC1.[CH3:14][CH2:15]N(CC)CC.C[Si](C#C)(C)C>C(Cl)Cl.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>[C:9]([C:2]1[CH:7]=[CH:6][C:5]([C:14]#[CH:15])=[CH:4][CH:3]=1)#[CH:13]

参加物

8

反応物 4

HCID 8028TetrahydrofuranHCID 8471TriethylamineHCID 12208p-DiiodobenzeneHCID 66111Trimethylsilylacetylene

生成物 1

HCID 1204631,4-Diethynylbenzene

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 6344Dichloromethane溶媒

実験手順

Firstly, a mixture of 1,4-diiodobenzene (4 g, 12.1 mmol), PdCl2(PPh3)2 (340 mg, 0.484 mmol) and CuI (92.4 mg, 0.484 mmol), was added with dist. THF (20 mL), dist. Et3N (60 mL) and trimethylsilylacetylene (3.77 mL, 26.7 mmol). The resultant mixture was stirred under a nitrogen atmosphere at 80° C. for 22 hours to obtain a reaction mixture. Then, the reaction mixture was diluted with CH2Cl2. After that, an organic layer was washed with sat. NaCl, and dried with MgSO4. The dried organic layer was filtered and concentrated to obtain a crude product. The obtained crude product was separated and purified by silica gel column chromatography (hexane/EtOAc=10/1) to obtain 1,4-diethynylbenzene.

後処理

  1. additionwas added with dist
  2. customto obtain a reaction mixture
  3. washAfter that, an organic layer was washed with sat. NaCl
  4. dry with materialdried with MgSO4
  5. filtrationThe dried organic layer was filtered
  6. concentrationconcentrated
  7. customto obtain a crude product
  8. customThe obtained crude product
  9. customwas separated
  10. custompurified by silica gel column chromatography (hexane/EtOAc=10/1)

出典と根拠

ORDレコード
ord-6034d2caa9fe431b851a0cf58f3e4f58
出典データセット
uspto-grants-2011_11
特許番号
US08053588B2

関連ノート

読み込み中…