Ethyl Acetate → HCID 86680926, compound

HRID 2168853Notes

Reaction equation

HRID 2168853 reaction equation
BrC1C=CC(CCCO)=CC=1.[C:12]([C:14]1[CH:15]=[C:16]2[C:21](=[CH:22][CH:23]=1)[CH:20]=[C:19]([O:24][Si:25]([CH:32]([CH3:34])[CH3:33])([CH:29]([CH3:31])[CH3:30])[CH:26]([CH3:28])[CH3:27])[CH:18]=[CH:17]2)#[CH:13].C(OCC)(=O)C>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:29]([Si:25]([CH:26]([CH3:27])[CH3:28])([CH:32]([CH3:34])[CH3:33])[O:24][C:19]1[CH:18]=[CH:17][C:16]2[C:21](=[CH:22][CH:23]=[C:14]([C:12]#[C:13][Si:25]([CH3:32])([CH3:29])[CH3:26])[CH:15]=2)[CH:20]=1)([CH3:31])[CH3:30]

Participants

8

Reactant 3

HCID 8857Ethyl AcetateHCID 105606143-(4-Bromophenyl)propan-1-olHCID 86680927HCID 86680927, 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

7.0 g (32.5 mmol) of 3-(4-bromophenyl)propan-1-ol are initially introduced in 70 ml of THF and 30 ml of diisopropylamine, and, after addition of 1.0 g (1.4 mmol) of bis(triphenylphosphine)palladium(II) chloride and 0.4 g (2.1 mmol) of copper(I) iodide, 16.4 g (50.5 mmol) of (6-ethynylnaphthalen-2-yloxy)triisopropylsilane in 30 ml of THF are added dropwise at 70° C. The batch is left to stir for 5 h at 70° C., 200 ml of ethyl acetate are added, and the mixture is washed three times with water. The combined aqueous phases are extracted with ethyl acetate, and the combined org. phases are dried over sodium sulfate and evaporated in vacuo. Chromatography of the crude product on silica gel with firstly toluene and then toluene/ethyl acetate (7:3) gives 2-triisopropylsilanyloxy-6-trimethylsilanylethynylnaphthalene as a brown oil, 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. extractionThe combined aqueous phases are extracted with ethyl acetate
  5. dry with materialphases are dried over sodium sulfate
  6. customevaporated in vacuo

Sources & evidence

ORD record
ord-d58468698a4446649755abffa94ef882
Source dataset
uspto-grants-2015_06
Patent number
US09045683B2

Reaction notes

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