Tetrahydrofuran → 1-Ethynyl-4-(hexyloxy)benzene

HRID 634529Notes

Reaction equation

HRID 634529 reaction equation
[CH2:1]([O:7][C:8]1[CH:13]=[CH:12][C:11]([C:14]#[C:15][Si](C)(C)C)=[CH:10][CH:9]=1)[CH2:2][CH2:3][CH2:4][CH2:5][CH3:6].C1COCC1.C([O-])([O-])=O.[K+].[K+]>CO>[C:14]([C:11]1[CH:12]=[CH:13][C:8]([O:7][CH2:1][CH2:2][CH2:3][CH2:4][CH2:5][CH3:6])=[CH:9][CH:10]=1)#[CH:15]

Participants

5

Reactant 3

HCID 8028TetrahydrofuranHCID 11430Potassium CarbonateHCID 85701272((4-(Hexyloxy)phenyl)ethynyl)trimethylsilane

Product 1

HCID 27751171-Ethynyl-4-(hexyloxy)benzene

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Procedure

To a 500 mL round bottom flask was added ((4-(hexyloxy)phenyl)ethynyl)trimethylsilane, 6, (14.95 g, 54.7 mmol, 1.0 equiv.) followed by THF (100 mL, 0.5 M), MeOH (100 mL, 0.5 M) and saturated aqueous K2CO3 (100 mL, 0.5 M). The mixture was stirred rapidly at room temperature for 4 hours. After 4 hours, the mixture was diluted with hexanes and rinsed with H2O (3×). The organic layer was dried with MgSO4 and the organics were filtered through a thin SiO2 pad with 5% ethyl acetate/95% hexanes to give 1-ethynyl-4-(hexyloxy)benzene, 3, as a clear oil (10.9 g, 54.2 mmol, 99%). 1H NMR (400 MHz, CDCl3) δ 7.45 (d, J=8.8 Hz, 2H), 6.86 (d, J=8.8 Hz, 2H), 3.99 (t, J=6.4 Hz, 2H), 3.02 (s, 1H), 1.81 (ap. p, J=8.0 Hz, 2H), 1.53-1.40 (m, 2H), 1.40-1.32 (m, 4H), 0.94 (t, J=7.2 Hz, 3H).

Workup

  1. waitAfter 4 hours
  2. washrinsed with H2O (3×)
  3. dry with materialThe organic layer was dried with MgSO4
  4. filtrationthe organics were filtered through a thin SiO2 pad with 5% ethyl acetate/95% hexanes

Sources & evidence

ORD record
ord-b2276731ff0e46ddb053070892bfcd3d
Source dataset
uspto-grants-2016_04
Patent number
US09324505B2

Reaction notes

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