Water → N,N-dibutyl-4-ethynylaniline

HRID 2369632Notes

Reaction equation

HRID 2369632 reaction equation
[OH-].[K+].C[Si]([C:7]#[C:8][C:9]1[CH:23]=[CH:22][C:12]([N:13]([CH2:18][CH2:19][CH2:20][CH3:21])[CH2:14][CH2:15][CH2:16][CH3:17])=[CH:11][CH:10]=1)(C)C.O>CO>[C:8]([C:9]1[CH:23]=[CH:22][C:12]([N:13]([CH2:18][CH2:19][CH2:20][CH3:21])[CH2:14][CH2:15][CH2:16][CH3:17])=[CH:11][CH:10]=1)#[CH:7]

Participants

5

Reactant 3

HCID 962WaterHCID 14797Potassium HydroxideHCID 12079525Benzenamine, N,N-dibutyl-4-[(trimethylsilyl)ethynyl]-

Product 1

HCID 12249159N,N-dibutyl-4-ethynylanilineYield 112.6%

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Procedure

Potassium hydroxide (5 mL, 2 M) was added to a solution of 4-trimethysilylethynyl-N,N-dibutylaniline (3 g, 9.1 mmol) in MeOH (100 mL) with stirring. The solution was stirred at 40° C. for 0.5 h, poured into water (200 mL), extracted with Et2O (3×50 mL), washed with water (50 mL), dried (MgSO4) and the solvent removed under reduced pressure to give the title compound (2.35 g, 100%) as a brown oil.

Workup

  1. stirringThe solution was stirred at 40° C. for 0.5 h
  2. extractionextracted with Et2O (3×50 mL)
  3. washwashed with water (50 mL)
  4. dry with materialdried (MgSO4)
  5. customthe solvent removed under reduced pressure

Sources & evidence

ORD record
ord-41ae0828225442c5a8ba3d53f5d058e6
Source dataset
uspto-grants-2014_04
Patent number
US08703978B2

Reaction notes

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