Tetrabutylammonium Fluoride → 2-(5-ethynyl-3-pyridyloxy)-N-(4-methylpent-2-yn-4-yl)butyramide

HRID 1374921Notes

Reaction equation

HRID 1374921 reaction equation
C[Si]([C:5]#[C:6][C:7]1[CH:8]=[C:9]([O:13][CH:14]([CH2:24][CH3:25])[C:15]([NH:17][C:18]([CH3:23])([CH3:22])[C:19]#[C:20][CH3:21])=[O:16])[CH:10]=[N:11][CH:12]=1)(C)C.[F-].C([N+](CCCC)(CCCC)CCCC)CCC.C(OCC)C.CCCCCC>ClCCl.O1CCCC1>[C:6]([C:7]1[CH:8]=[C:9]([O:13][CH:14]([CH2:24][CH3:25])[C:15]([NH:17][C:18]([CH3:23])([CH3:22])[C:19]#[C:20][CH3:21])=[O:16])[CH:10]=[N:11][CH:12]=1)#[CH:5]

Participants

6

Reactant 3

HCID 2724141Tetrabutylammonium FluorideHCID 210784012-(5-trimethylsilylethynyl-3-pyridyloxy)-N-(4-methylpent-2-yn-4-yl)butyramideHCID 21584099Diethylether hexane

Product 1

HCID 210783982-(5-ethynyl-3-pyridyloxy)-N-(4-methylpent-2-yn-4-yl)butyramide

Reagents, catalysts & solvents 2

HCID 6344DichloromethaneSolvent2×HCID 8028TetrahydrofuranSolvent

Procedure

The product from Stage 1 (0.4 g) was dissolved in dichloromethane (10 ml) with stirring and a solution of tetra n-butylammonium fluoride in tetrahydrofuran (1.4 ml, 1M) was added. The mixture was stirred at ambient temperature for 2 hours then stored for 18 hours. Further dichloromethane was added and the organic phase was washed with water (twice), dried over magnesium sulphate and evaporated under reduced pressure to give a gum that was fractionated by chromatography (silica; diethyl ether/hexane, 2:1 by volume) to give the required product, 0.21 g, as a pale brown oil.

Workup

  1. stirringThe mixture was stirred at ambient temperature for 2 hours
  2. washthe organic phase was washed with water (twice),
  3. dry with materialdried over magnesium sulphate
  4. customevaporated under reduced pressure
  5. customto give a gum that

Sources & evidence

ORD record
ord-6ec130d766524b81ba413f0c3c23ed0b
Source dataset
uspto-grants-2007_01
Patent number
US07166621B2

Reaction notes

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