Diethyl Ether → HCID 86680926, compound

HRID 2168852Notes

Reaction equation

HRID 2168852 reaction equation
Br[C:2]1[CH:3]=[C:4]2[C:9](=[CH:10][CH:11]=1)[CH:8]=[C:7]([O:12][Si:13]([CH:20]([CH3:22])[CH3:21])([CH:17]([CH3:19])[CH3:18])[CH:14]([CH3:16])[CH3:15])[CH:6]=[CH:5]2.[CH3:23][Si:24]([C:27]#[CH:28])([CH3:26])[CH3:25].CCOCC>C1COCC1.C(NC(C)C)(C)C.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>[CH:20]([Si:13]([CH:14]([CH3:16])[CH3:15])([CH:17]([CH3:18])[CH3:19])[O:12][C:7]1[CH:6]=[CH:5][C:4]2[C:9](=[CH:10][CH:11]=[C:2]([C:28]#[C:27][Si:24]([CH3:26])([CH3:25])[CH3:23])[CH:3]=2)[CH:8]=1)([CH3:22])[CH3:21]

Participants

8

Reactant 3

HCID 3283Diethyl EtherHCID 66111TrimethylsilylacetyleneHCID 59245569HCID 59245569, compound

Product 1

HCID 86680926HCID 86680926, compound

Reagents, catalysts & solvents 4

HCID 24350Copper(1+) iodide; Copper(I) iodide; Cuprous iodide; Cuprous iodide (CuI)CatalystHCID 178418476HCID 178418476, compoundCatalystHCID 7912DiisopropylamineSolventHCID 8028TetrahydrofuranSolvent2×

Conditions

Temperature
70 °C

Procedure

35.0 g (90.4 mmol) of (6-bromonaphthalen-2-yloxy)triisopropylsilane are initially introduced in 120 ml of THF and 70 ml of diisopropylamine, and, after addition of 3.50 g (5.0 mmol) of bis(triphenylphosphine)palladium(II) chloride and 1.0 g (5.3 mmol) of copper(I) iodide, 25.0 g (0.255 mol) of trimethylsilylacetylene in 30 ml of THF are added dropwise at 70° C. The batch is left to stir for 4 h at 70° C. and overnight at room temp., 150 ml of MTB ether are added, and the mixture is washed three times with water, dried over sodium sulfate and evaporated in vacuo. Filtration of the crude product through silica gel with heptane gives 2-triisopropylsilanyloxy-6-trimethylsilanylethynylnaphthalene, which is employed in the next step without further purification.

Workup

  1. additionare added dropwise at 70° C
  2. waitThe batch is left
  3. washthe mixture is washed three times with water
  4. dry with materialdried over sodium sulfate
  5. customevaporated in vacuo
  6. filtrationFiltration of the crude product through silica gel with heptane

Sources & evidence

ORD record
ord-6706c59603f840698eedd2164f9ef4b0
Source dataset
uspto-grants-2015_06
Patent number
US09045683B2

Reaction notes

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