Triethylamine → p-(Triethylsilyl)ethynyl phenol

HRID 33735Notes

Reaction equation

HRID 33735 reaction equation
[CH2:1]([Si:3]([C:8]#[CH:9])([CH2:6][CH3:7])[CH2:4][CH3:5])[CH3:2].I[C:11]1[CH:16]=[CH:15][C:14]([OH:17])=[CH:13][CH:12]=1.C(N(CC)CC)C>CN(C=O)C.[Cu]I>[CH2:8]([Si:3]([C:6]#[C:7][C:11]1[CH:16]=[CH:15][C:14]([OH:17])=[CH:13][CH:12]=1)([CH2:4][CH3:5])[CH2:1][CH3:2])[CH3:9]

Participants

6

Reactant 3

HCID 8471TriethylamineHCID 108944-IodophenolHCID 637947(Triethylsilyl)acetylene

Product 1

HCID 22644432p-(Triethylsilyl)ethynyl phenol

Reagents, catalysts & solvents 2

HCID 24350Copper(1+) iodide; Copper(I) iodide; Cuprous iodide; Cuprous iodide (CuI)CatalystHCID 6228DimethylformamideSolvent

Procedure

Triethylsilylacetylene 108 (3 eq.) was coupled to 4-iodophenol 107 (1 eq.) in the presence of CuI (0.05 eq.), Pd[PPh3]4 (0.05 eq.), and triethylamine (2 eq.) in DMF. The mixture was stirred at ambient temperature for 5 hours after which it was concentrated under vacuum to afford a crude black oil. The oil was purified by flash column chromatography to afford pure p-(triethylsilyl)ethynyl phenol 109.

Workup

  1. concentrationwas concentrated under vacuum
  2. customto afford a crude black oil
  3. customThe oil was purified by flash column chromatography

Sources & evidence

ORD record
ord-09850c3b7c7744fb8d0d7d1ff3e4dbe5
Source dataset
uspto-grants-2008_09
Patent number
US07429651B2

Reaction notes

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