Tetrahydrofuran → HCID 59806151, compound

HRID 556138Notes

Reaction equation

HRID 556138 reaction equation
I[C:2]1[CH:7]=[CH:6][C:5]([C:8]#[C:9][C:10]2[CH:15]=[CH:14][C:13](I)=[CH:12][CH:11]=2)=[CH:4][CH:3]=1.[CH2:17]1[CH2:21]OCC1.CCN(CC)CC.[CH3:29][Si:30]([C:33]#[CH:34])([CH3:32])[CH3:31]>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>[CH3:29][Si:30]([C:33]#[C:34][C:2]1[CH:7]=[CH:6][C:5]([C:8]#[C:9][C:10]2[CH:15]=[CH:14][C:13]([C:21]#[C:17][Si:30]([CH3:32])([CH3:31])[CH3:29])=[CH:12][CH:11]=2)=[CH:4][CH:3]=1)([CH3:32])[CH3:31]

Participants

8

Reactant 4

HCID 8028TetrahydrofuranHCID 8471TriethylamineHCID 66111TrimethylsilylacetyleneHCID 11048257Bis(4-iodophenyl)acetylene

Product 1

HCID 59806151HCID 59806151, compound

Reagents, catalysts & solvents 3

HCID 24350Copper(1+) iodide; Copper(I) iodide; Cuprous iodide; Cuprous iodide (CuI)CatalystHCID 178418476HCID 178418476, compoundCatalystHCID 6344DichloromethaneSolvent

Procedure

Firstly, a mixture of 4,4′-diiodotolan (171 mg, 0.40 mmol), PdCl2(PPh3)2 (27.9 mg, 0.040 mmol) and CuI (7.6 mg, 0.040 mmol) was added with dist. THF (3 mL), dist. Et3N (3 mL) and trimethylsilylacetylene (140 μL, 0.99 mmol). The resultant mixture was then stirred under a nitrogen atmosphere at 50° C. for 17 hours to obtain a reaction mixture. Subsequently, the reaction mixture was diluted with CH2Cl2. After that, an organic layer was washed with sat. NaCl, and the washed organic layer was then dried with MgSO4. The dried organic layer was filtered and concentrated to obtain a crude product (I). The obtained crude product (I) was separated and purified by silica gel column chromatography (hexane/EtOAc=10/1) to obtain 4,4′-bis(trimethylsilylethynyl)tolan.

Workup

  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 materialthe washed organic layer was then dried with MgSO4
  5. filtrationThe dried organic layer was filtered
  6. concentrationconcentrated
  7. customto obtain a crude product (I)
  8. customThe obtained crude product (I)
  9. customwas separated
  10. custompurified by silica gel column chromatography (hexane/EtOAc=10/1)

Sources & evidence

ORD record
ord-315e6b72c12c4ae9b03e85e5115c85fc
Source dataset
uspto-grants-2011_11
Patent number
US08053588B2

Reaction notes

Loading…