Tetrahydrofuran → 1,4-Diethynylbenzene

HRID 556136노트

반응식

HRID 556136 반응식
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]

참가 물질

8

반응물 4

HCID 8028TetrahydrofuranHCID 8471TriethylamineHCID 12208p-DiiodobenzeneHCID 66111Trimethylsilylacetylene

생성물 1

HCID 1204631,4-Diethynylbenzene

시약·촉매·용매 3

HCID 24350Copper(1+) iodide; Copper(I) iodide; Cuprous iodide; Cuprous iodide (CuI)촉매HCID 178418476HCID 178418476, 화합물촉매HCID 6344Dichloromethane용매

실험 절차

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.

후처리

  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)

출처 및 근거

ORD 기록
ord-6034d2caa9fe431b851a0cf58f3e4f58
출처 데이터셋
uspto-grants-2011_11
특허 번호
US08053588B2

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