Tetrahydrofuran → HCID 131729268, compound

HRID 556130Notes

Reaction equation

HRID 556130 reaction equation
[CH2:1]([CH:4]([CH2:15][CH:16]=[CH2:17])[CH2:5][O:6][SiH2:7][C:8]1[CH:13]=[CH:12][C:11](I)=[CH:10][CH:9]=1)[CH:2]=[CH2:3].C1COCC1.CCN(CC)CC.[CH3:30][C:31]([OH:38])([CH2:34][CH:35]([CH3:37])[CH3:36])[C:32]#[CH:33]>CCOCC.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>[CH2:1]([CH:4]([CH2:15][CH:16]=[CH2:17])[CH2:5][O:6][SiH2:7][C:8]1[CH:13]=[CH:12][C:11]([C:33]#[C:32][C:31]([CH3:30])([OH:38])[CH2:34][CH:35]([CH3:37])[CH3:36])=[CH:10][CH:9]=1)[CH:2]=[CH2:3]

Participants

8

Reactant 4

HCID 8028TetrahydrofuranHCID 8471TriethylamineHCID 610183,5-Dimethyl-1-hexyn-3-olHCID 131727682HCID 131727682, compound

Product 1

HCID 131729268HCID 131729268, compoundYield 88.3%

Reagents, catalysts & solvents 3

HCID 24350Copper(1+) iodide; Copper(I) iodide; Cuprous iodide; Cuprous iodide (CuI)CatalystHCID 178418476HCID 178418476, compoundCatalystHCID 3283Diethyl EtherSolvent

Procedure

Firstly, a mixture of 4-(diallylethoxysilyl)iodobenzene (147 mg, 0.41 mmol), PdCl2(PPh3)2 (11.5 mg, 0.016 mmol) and CuI (3.1 mg, 0.016 mmol) was added with dist. THF (2 mL), dist. Et3N (3 mL) and 3,5-dimethyl-1-hexyn-3-ol (79 μL, 0.54 mmol). The resultant mixture was stirred under a nitrogen atmosphere at 50° C. for 3 hours to obtain a reaction mixture. Then, the reaction mixture was diluted with ether, and an organic layer was washed with dist. H2O and sat. NaCl. After that, the organic layer was dried with MgSO4, and the dried organic layer was then filtered and concentrated to obtain a crude product. The obtained crude product was separated and purified by silica gel column chromatography (hexane/EtOAc=5/1) to obtain 1-(diallylethoxysilyl)-4-(3,5-dimethyl-3-hydroxy-hexynyl)benzene (129.1 mg, 88% yield).

Workup

  1. additionwas added with dist
  2. customto obtain a reaction mixture
  3. washan organic layer was washed with dist
  4. dry with materialAfter that, the organic layer was dried with MgSO4
  5. filtrationthe dried organic layer was then 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=5/1)

Sources & evidence

ORD record
ord-da747e7e00fb48a190414db302de5b16
Source dataset
uspto-grants-2011_11
Patent number
US08053588B2

Reaction notes

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