Methanol → 4'-Diethylaminophenyl acetylene

HRID 1618885Notes

Reaction equation

HRID 1618885 reaction equation
[CH2:1]([N:3]([C:6]1[CH:11]=[CH:10][C:9]([C:12]#[C:13][Si](C)(C)C)=[CH:8][CH:7]=1)[CH2:4][CH3:5])[CH3:2].C([O-])([O-])=O.[K+].[K+].CO>O>[CH2:1]([N:3]([C:6]1[CH:7]=[CH:8][C:9]([C:12]#[CH:13])=[CH:10][CH:11]=1)[CH2:4][CH3:5])[CH3:2]

Participants

5

Reactant 3

HCID 887MethanolHCID 11430Potassium CarbonateHCID 59180882HCID 59180882, compound

Product 1

HCID 114352194'-Diethylaminophenyl acetylene

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Conditions

Temperature
65 °C

Procedure

A mixture of N,N-diethyl-(4-trimethylsilanylethynyl-phenyl)amine (500 mg 2.03 mmol), K2CO3 (1.5 g 10.8 mmol) and methanol (30 mL) was stirred at 65° C. for 30 h. The reaction mixture was cooled, poured into water and extracted with ethyl acetate (50×3). The combined extract was dried over anhydrous MgSO4. The solvent was removed under reduced pressure and the crude material was further purified by filtration through a short silica gel column with hexane/EAC (0-5%) and the product separated as a semi solid. Yield: 250 mg (72.2%) IR (neat) 2971, 2098, 1607, 1551 cm−1; 1H NMR (400 MHz, CDCl3) δ7.36 (d, J=8.4 Hz, 2H), 6.59 (d, J=8.4 Hz, 2H), 3.36 (q, J=6.8 Hz, 4H), 1.16 (t, 6.8 Hz, 6H); 13CNMR (100 MHz, CDCl3) δ 147.68, 133.31, 110.90, 107.46, 84.96, 74.38, 44.19, 12.41.

Workup

  1. temperatureThe reaction mixture was cooled
  2. extractionextracted with ethyl acetate (50×3)
  3. extractionThe combined extract
  4. dry with materialwas dried over anhydrous MgSO4
  5. customThe solvent was removed under reduced pressure
  6. filtrationthe crude material was further purified by filtration through a short silica gel column with hexane/EAC (0-5%)
  7. customthe product separated as a semi solid

Sources & evidence

ORD record
ord-b4415c697360414dba4e057f1a1f8703
Source dataset
uspto-grants-2014_07
Patent number
US08772048B2

Reaction notes

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