Tetrabutylammonium Fluoride → 2-(6-quinolinyloxy)-N-(1-hydroxy-4-methylpent-2-yn-4-yl) butyramide

HRID 1244805Notes

Reaction equation

HRID 1244805 reaction equation
[N:1]1[C:10]2[C:5](=[CH:6][C:7]([O:11][CH:12]([CH2:30][CH3:31])[C:13]([NH:15][C:16]([CH3:29])([CH3:28])[C:17]#[C:18][CH:19]([O:24][SiH](C)C)C(C)(C)C)=[O:14])=[CH:8][CH:9]=2)[CH:4]=[CH:3][CH:2]=1.[F-].C([N+](CCCC)(CCCC)CCCC)CCC.CCCCCC.C(OCC)(=O)C>O1CCCC1>[N:1]1[C:10]2[C:5](=[CH:6][C:7]([O:11][CH:12]([CH2:30][CH3:31])[C:13]([NH:15][C:16]([CH3:28])([CH3:29])[C:17]#[C:18][CH2:19][OH:24])=[O:14])=[CH:8][CH:9]=2)[CH:4]=[CH:3][CH:2]=1

Participants

5

Reactant 3

HCID 2724141Tetrabutylammonium FluorideHCID 21226206Ethyl acetate hexaneHCID 131725990N-(5-dimethylsilyloxy-2,6,6-trimethylhept-3-yn-2-yl)-2-quinolin-6-yloxybutanamide

Product 1

HCID 116312392-(6-quinolinyloxy)-N-(1-hydroxy-4-methylpent-2-yn-4-yl) butyramideYield 69.8%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Conditions

Temperature
0 °C

Procedure

2-(6-Quinolinyloxy)-N-(1-tert.butyldimethylsilyloxy-4-methylpent-2-yn-4-yl)butyramide (0.58 g) in tetrahydrofuran (10 ml) was stirred at 3–5° C. and a solution of tetra n-butylammonium fluoride (2.64 ml of 1M solution in tetrahydrofuran) was added dropwise over 5 minutes. On completion of addition, the mixture was stirred for 0.5 hour at 0° C., 0.75 hour at ambient temperature then 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 gum that was fractionated by chromatography (silica; hexane/ethyl acetate, 1:2 by volume) to give the required product as a colourless glass (0.30 g).

Workup

  1. additionOn completion of addition
  2. waitthen stored 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 gum that

Sources & evidence

ORD record
ord-a39323f1e5a34b3c9f66d0153f1f4bdb
Source dataset
uspto-grants-2006_10
Patent number
US07122672B2

Reaction notes

Loading…