Tetrabutylammonium Fluoride → HCID 68849778, compound

HRID 29219Notes

Reaction equation

HRID 29219 reaction equation
[Cl:1][C:2]1[CH:3]=[C:4]([CH:26]=[C:27]([Cl:29])[CH:28]=1)[O:5][CH:6]([CH2:24][CH3:25])[C:7]([NH:9][C:10]([CH3:23])([CH3:22])[C:11]#[C:12][CH2:13]O[Si](C(C)(C)C)(C)C)=[O:8].[F-].C([N+](CCCC)(CCCC)CCCC)CCC.CCCCCC.[C:54](OCC)(=[O:56])C>O1CCCC1>[Cl:29][C:27]1[CH:26]=[C:4]([CH:3]=[C:2]([Cl:1])[CH:28]=1)[O:5][CH:6]([CH2:24][CH3:25])[C:7]([NH:9][C:10]([CH3:22])([CH3:23])[C:11]#[C:12][CH2:13][CH2:54][OH:56])=[O:8]

Participants

5

Reactant 3

HCID 2724141Tetrabutylammonium FluorideHCID 21226206Ethyl acetate hexaneHCID 68848288HCID 68848288, compound

Product 1

HCID 68849778HCID 68849778, compound

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Conditions

Temperature
0 °C

Procedure

2-(3,5-Dichlorophenoxy)-N-(1-tert-butyldimethylsilyloxy-4-methylpent-2-yn-4-yl)butyramide (prepared as described in Example 1; 3.35 g) in tetrahydrofuran (60 ml) was stirred at 3-5° C. and a solution of tetra n-butylammonium fluoride (14.6 ml of 1M solution in tetrahydrofuran) was added dropwise over 5 minutes. On completion of the addition, the mixture was stirred for 0.5 hour at 0° C., 2 hours at ambient temperature and stored for 18 hours. The solvent was evaporated under reduced pressure and the residue partitioned between ethyl acetate and aqueous ammonium chloride. The organic phase was separated, washed with aqueous ammonium chloride, brine, dried over magnesium sulphate and evaporated under reduced pressure to give a colourless solid that was fractionated by chromatography (silica; hexane/ethyl acetate, 2:1 by volume) to give the required product as a colourless solid (2.01 g) mp 104-106° C.

Workup

  1. additionOn completion of the addition
  2. waitstored for 18 hours
  3. customThe solvent was evaporated under reduced pressure
  4. customthe residue partitioned between ethyl acetate and aqueous ammonium chloride
  5. customThe organic phase was separated
  6. washwashed with aqueous ammonium chloride, brine
  7. dry with materialdried over magnesium sulphate
  8. customevaporated under reduced pressure
  9. customto give a colourless solid

Sources & evidence

ORD record
ord-7dc3257db63a4c8a8065ba0579f32dac
Source dataset
uspto-grants-2008_09
Patent number
US07420090B2

Reaction notes

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