Potassium Carbonate → 1-Ethynyl-4-(4-n-butylphenylethynyl)benzene

HRID 2367908Notes

Reaction equation

HRID 2367908 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]([CH2:21][CH2:22][CH2:23][CH3:24])=[CH:17][CH:16]=2)=[CH:9][CH:8]=1)(C)C.C([O-])([O-])=O.[K+].[K+]>C(Cl)Cl.CO>[C:6]([C:7]1[CH:12]=[CH:11][C:10]([C:13]#[C:14][C:15]2[CH:16]=[CH:17][C:18]([CH2:21][CH2:22][CH2:23][CH3:24])=[CH:19][CH:20]=2)=[CH:9][CH:8]=1)#[CH:5]

Participants

5

Reactant 2

HCID 11430Potassium CarbonateHCID 66776559HCID 66776559, compound

Product 1

HCID 858121891-Ethynyl-4-(4-n-butylphenylethynyl)benzeneYield 8.2%

Reagents, catalysts & solvents 2

HCID 887MethanolSolventHCID 6344DichloromethaneSolvent

Procedure

1-(trimethylsilylethynyl)-4-(4-n-butylphenylethynyl)benzene (192 g, 11.86 mmol) was dissolved in CH2Cl2 (100 nit) diluted with MeOH (40 mL) and then treated with powdered K2CO3 (2.1 g, 15 mmol) and allowed to stir at ambient temperature for 19 h under N2. The reaction mixture was filtered to remove solids, concentrated, redissolved in CHCl3, washed with water (2×), brine, dried over MgSO4, filtered and concentrated to dryness to give a brown solid. The solid was chromatographed on silica gel, eluting with 15:1 hexanes/EtOAc to give several fractions rich in product. These fractions were combined and chromatographed again with 95:5 hexanes/EtOAc to give 0.25 g (7%) product as a waxy solid. 1H NMR (CDCl3) δ: 7.50 (s, 4H), 7.47 (d, 8.2 Hz, 2H); 7.21 (d, J=8.2 Hz, 2H); 3.20 (s, 1H); 2.63 (t, J=7.8 Hz, 2H); 1.64 (m, 2H); 1.41 (m, 2H); 0.97 (t, J=7.5 Hz, 3H). 13C{1H} NMR (CDCl3): 143.8, 132.1, 11.6, 131.4, 1128.6, 124.1, 121.6, 120.0, 911.7, 88.2, 83.4, 78.8, 35.6, 33.4, 22.2, 14.0 ppm.

Workup

  1. filtrationThe reaction mixture was filtered
  2. customto remove solids
  3. concentrationconcentrated
  4. dissolutionredissolved in CHCl3
  5. washwashed with water (2×), brine
  6. dry with materialdried over MgSO4
  7. filtrationfiltered
  8. concentrationconcentrated to dryness
  9. customto give a brown solid
  10. customThe solid was chromatographed on silica gel
  11. washeluting with 15:1 hexanes/EtOAc
  12. customto give several fractions rich in product
  13. customchromatographed again with 95:5 hexanes/EtOAc

Sources & evidence

ORD record
ord-46308107442f4c5c835c82a6d63cdb95
Source dataset
uspto-grants-2014_04
Patent number
US08703388B2

Reaction notes

Loading…