Water → (1-Benzofuran-2-ylethynyl)(trimethyl)silane

HRID 2377286Notes

Reaction equation

HRID 2377286 reaction equation
I[C:2]1[O:3][C:4]2[CH:10]=[CH:9][CH:8]=[CH:7][C:5]=2[CH:6]=1.[CH3:11][Si:12]([C:15]#[CH:16])([CH3:14])[CH3:13].C(NC(C)C)(C)C.O>O1CCCC1.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)I>[O:3]1[C:4]2[CH:10]=[CH:9][CH:8]=[CH:7][C:5]=2[CH:6]=[C:2]1[C:16]#[C:15][Si:12]([CH3:14])([CH3:13])[CH3:11]

Participants

8

Reactant 4

HCID 962WaterHCID 7912DiisopropylamineHCID 66111TrimethylsilylacetyleneHCID 138317942-Iodo-1-benzofuran

Product 1

HCID 25096393(1-Benzofuran-2-ylethynyl)(trimethyl)silane

Reagents, catalysts & solvents 3

HCID 83717Copper iodideCatalystHCID 178418476HCID 178418476, compoundCatalystHCID 8028TetrahydrofuranSolvent

Procedure

A solution of Example 651 (1.00 g, 4.10 mmol), (trimethylsilyl)acetylene (0.80 mL, 5.68 mmol), dichlorobis(triphenylphosphine)palladium(II) (49 mg, 0.13 mmol), diisopropylamine (1.08 mL, 7.74 mmol) and copper iodide (3 mg, 0.258 mmol) in tetrahydrofuran (5 mL) was stirred at room temperature for about 16 h. The solution was poured into water and was extracted with dichloromethane. The combined organic extracts were washed with brine, dried (MgSO4), filtered and concentrated under vacuum. The residue was purified by flash column chromatography on silica gel using hexane/ethyl acetate (9:1) as eluent to provide Example 652. 1H NMR (300 MHz, CDCl3) δ 0.29 (m, 9H), 6.94 (s, 1H), 7.23 (m, 1H), 7.33 (m, 1H), 7.43 (m, 1H), 7.54 (d, J=7.8 Hz, 1H).

Workup

  1. extractionwas extracted with dichloromethane
  2. washThe combined organic extracts were washed with brine
  3. dry with materialdried (MgSO4)
  4. filtrationfiltered
  5. concentrationconcentrated under vacuum
  6. customThe residue was purified by flash column chromatography on silica gel
  7. customto provide Example 652

Sources & evidence

ORD record
ord-e8e43179aad64aa4bd8894c7b1c97158
Source dataset
uspto-grants-2008_12
Patent number
US07468371B2

Reaction notes

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