Methanol → 1-Ethynyl-4-[(4-methylphenyl)ethynyl]benzene

HRID 1644143Notes

Reaction equation

HRID 1644143 reaction equation
C[Si]([C:5]#[C:6][C:7]1[CH:12]=[CH:11][C:10]([C:13]#[C:14][C:15]2[CH:20]=[CH:19][C:18]([CH3:21])=[CH:17][CH:16]=2)=[CH:9][CH:8]=1)(C)C.C(=O)([O-])[O-].[K+].[K+].CO>C(Cl)Cl>[C:6]([C:7]1[CH:12]=[CH:11][C:10]([C:13]#[C:14][C:15]2[CH:16]=[CH:17][C:18]([CH3:21])=[CH:19][CH:20]=2)=[CH:9][CH:8]=1)#[CH:5]

Participants

5

Reactant 3

HCID 887MethanolHCID 11430Potassium CarbonateHCID 66777028Trimethyl({4-[(4-methylphenyl)ethynyl]phenyl}ethynyl)silane

Product 1

HCID 229664951-Ethynyl-4-[(4-methylphenyl)ethynyl]benzeneYield 73.1%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

Into a 100 ml round bottom flask was placed a mixture of 1.43 g (0.005 mole) of 1-(trimethylsilylethynyl)-4-(4-methylphenylethynyl)benzene, 1.37 g (0.01 mole) potassium carbonate, 20 ml of methanol and 20 ml of methylene chloride. The mixture was stirred at room temperature under nitrogen overnight. The dark brown suspension was filtered and the filtrate was washed twice with water (20 ml each). The aqueous layers were combined and extracted twice with methylene chloride (10 ml each). The methylene chloride layers were combined and dried over anhydrous MgSO4, filtered and concentrated. 0.7 g (73.1% yield) of brownish yellow solid was obtained. 1HNMR: 2.40 ppm (2,3H); 3.19 ppm (s, 1H); 7.15-7.18 ppm (d, 2H); 7.43-7.46 ppm (d, 2H); 7.49 (s, 4H). The NMR indicated that there were some by-products present. It was used for the next step without further purification.

Workup

  1. customInto a 100 ml round bottom flask was placed
  2. filtrationThe dark brown suspension was filtered
  3. washthe filtrate was washed twice with water (20 ml each)
  4. extractionextracted twice with methylene chloride (10 ml each)
  5. dry with materialdried over anhydrous MgSO4
  6. filtrationfiltered
  7. concentrationconcentrated

Sources & evidence

ORD record
ord-b2eb8badb2174eee817d741452147141
Source dataset
uspto-grants-2012_02
Patent number
US08124299B2

Reaction notes

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