Tetrabutylammonium Fluoride → HCID 18961685, compound

HRID 1707562Notes

Reaction equation

HRID 1707562 reaction equation
[C:1]([N:3]1[C:7](=[O:8])[C:6]([CH:10]([CH3:12])[CH3:11])([CH3:9])[N:5]=[C:4]1[C:13]1[N:27]=[CH:26][CH:25]=[CH:24][C:14]=1[C:15]([O:17]CC[Si](C)(C)C)=[O:16])#[N:2].[F-].[CH2:29]([N+:33]([CH2:42][CH2:43][CH2:44][CH3:45])([CH2:38][CH2:39][CH2:40][CH3:41])[CH2:34][CH2:35][CH2:36][CH3:37])[CH2:30][CH2:31][CH3:32]>O1CCCC1>[C:1]([N:3]1[C:7](=[O:8])[C:6]([CH:10]([CH3:12])[CH3:11])([CH3:9])[N:5]=[C:4]1[C:13]1[N:27]=[CH:26][CH:25]=[CH:24][C:14]=1[C:15]([O-:17])=[O:16])#[N:2].[CH2:42]([N+:33]([CH2:29][CH2:30][CH2:31][CH3:32])([CH2:34][CH2:35][CH2:36][CH3:37])[CH2:38][CH2:39][CH2:40][CH3:41])[CH2:43][CH2:44][CH3:45]

Participants

4

Reactant 2

HCID 2724141Tetrabutylammonium FluorideHCID 15029360HCID 15029360, compound

Product 1

HCID 18961685HCID 18961685, compoundYield 82.4%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

To a solution of 2-(trimethylsilyl)ethyl 2-(1-cyano-4-isopropyl-4-methyl-5-oxo-2-imidazolin-2-yl)nicotinate (7.74 g, 0.02 mol) and tetrahydrofuran is added tetrabutylammonium fluoride (0.020 mol, 1.0M, 20.0 mL). The reaction mixture is stirred at room temperature for 72 hours, concentrated in vacuo to an oil and the oil is dissolved into methylene chloride. The methylene chloride solution is washed sequentially with water and brine, dried over anhydrous magnesium sulfate and concentrated in vacuo to give the title compound as a dark yellow syrup (8.7 g, 82%), identified by IR and NMR spectral analyses.

Workup

  1. concentrationconcentrated in vacuo to an oil
  2. dissolutionthe oil is dissolved into methylene chloride
  3. washThe methylene chloride solution is washed sequentially with water and brine
  4. dry with materialdried over anhydrous magnesium sulfate
  5. concentrationconcentrated in vacuo

Sources & evidence

ORD record
ord-a3ea147ac18544ac9a2cc73056683e6c
Source dataset
uspto-grants-1994_10
Patent number
US05354727

Reaction notes

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