Tetrahydrofuran → 1,4-Diethynylbenzene

HRID 556136

Reaktionsgleichung

Reaktionsgleichung von HRID 556136
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]

Komponenten

8

Edukt 4

HCID 8028TetrahydrofuranHCID 8471TriethylamineHCID 12208p-DiiodobenzeneHCID 66111Trimethylsilylacetylene

Produkt 1

HCID 1204631,4-Diethynylbenzene

Reagenzien, Katalysatoren, Lösungsmittel 3

HCID 24350Copper(1+) iodide; Copper(I) iodide; Cuprous iodide; Cuprous iodide (CuI)KatalysatorHCID 178418476HCID 178418476, VerbindungKatalysatorHCID 6344DichloromethaneLösungsmittel

Versuchsvorschrift

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.

Aufarbeitung

  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)

Quellen und Nachweise

ORD-Eintrag
ord-6034d2caa9fe431b851a0cf58f3e4f58
Quelldatensatz
uspto-grants-2011_11
Patentnummer
US08053588B2

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