Methanol → HCID 87145781, compound

HRID 1644145Notes

Reaction equation

HRID 1644145 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]=[C:19]([O:21][CH3:22])[CH:18]=[C:17]([O:23][CH3:24])[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:8]=[CH:9][C:10]([C:13]#[C:14][C:15]2[CH:20]=[C:19]([O:21][CH3:22])[CH:18]=[C:17]([O:23][CH3:24])[CH:16]=2)=[CH:11][CH:12]=1)#[CH:5]

Participants

5

Reactant 3

HCID 887MethanolHCID 11430Potassium CarbonateHCID 66776054HCID 66776054, compound

Product 1

HCID 87145781HCID 87145781, compoundYield 63.4%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

Into a 100 ml round bottom flask was placed a mixture of 2.27 g (0.0068 mole) of 1-(trimethylsilylethynyl)-4-(3,5-dimethoxyphenylethynyl)benzene, 1.88 g (0.0136 mole) potassium carbonate, 30 ml of methanol and 30 ml of methylene chloride. The mixture was stirred at room temperature overnight under nitrogen. The dark brown suspension was filtered through an alumina bed to remove some color, and the still dark color filtrate was washed twice with water (30 ml each). The aqueous layers were combined and extracted twice with methylene chloride (20 ml each). The methylene chloride layers were combined and dried over anhydrous MgSO4, filtered and concentrated. 1.13 g of brown oil was obtained. The crude oil was purified by Preparative LC using 1:10 EtOAc:hexane as eluting solvent. 240 mg (13.5% yield) of yellow solid was obtained. 1HNMR: 3.20 ppm (s, 1H); 3.83 ppm (s, 6H); 6.50 ppm (t, 1H); 6.71 ppm (d, 2H); 7.50 ppm (s, 4H).

Workup

  1. customInto a 100 ml round bottom flask was placed
  2. filtrationThe dark brown suspension was filtered through an alumina bed
  3. customto remove some color
  4. washthe still dark color filtrate was washed twice with water (30 ml each)
  5. extractionextracted twice with methylene chloride (20 ml each)
  6. dry with materialdried over anhydrous MgSO4
  7. filtrationfiltered
  8. concentrationconcentrated

Sources & evidence

ORD record
ord-1088b123169f4618bbe8e28b9ebea7ed
Source dataset
uspto-grants-2012_02
Patent number
US08124299B2

Reaction notes

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