Ethyl trifluoroacetate → HCID 19983612, compound

HRID 1460282Notes

Reaction equation

HRID 1460282 reaction equation
[CH3:1][C:2]([CH3:17])([O:5][C:6]1[CH:11]=[CH:10][C:9]([O:12][C:13]([F:16])([F:15])[F:14])=[CH:8][CH:7]=1)[C:3]#[CH:4].C([Li])CCC.[F:23][C:24]([F:31])([F:30])[C:25](OCC)=[O:26].CCCCCC.C(OCC)C>O1CCCC1.O>[F:23][C:24]([F:31])([F:30])[C:25](=[O:26])[C:4]#[C:3][C:2]([CH3:17])([O:5][C:6]1[CH:11]=[CH:10][C:9]([O:12][C:13]([F:14])([F:15])[F:16])=[CH:8][CH:7]=1)[CH3:1]

Participants

7

Reactant 4

HCID 9794Ethyl trifluoroacetateHCID 150529171-[(2-Methylbut-3-yn-2-yl)oxy]-4-(trifluoromethoxy)benzeneHCID 21584099Diethylether hexaneHCID 178418339Butyllithium

Product 1

HCID 19983612HCID 19983612, compound

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 8028TetrahydrofuranSolvent

Procedure

To a solution of 1.47 g (6 mmol) of 1-(1,1-dimethyl-2-propynyloxy)-4-trifluoromethoxybenzene in 25 ml of tetrahydrofuran cooled to -78° C. is added 2.4 ml of n-butyllithium (2.5M in hexanes). The solution is maintained with stirring for 1 hour. The mixture is treated with 1.70 g (12 mmol, 1.43 ml) of ethyl trifluoroacetate at -78° C. and is allowed to warm to room temperature. After stirring for 1 hour, the mixture is diluted with water and is extracted with ethyl ether (3 times). The combined ethereal extracts are washed with aqueous sodium bicarbonate, dried over magnesium sulfate, filtered and evaporated to give a light oil. Flash chromatography using hexane:ethyl ether (65:35) affords the title compound: IR (film) 2215, 1740 cm-1 ; NMR (CDCl3) δ1.73 (6H, s), 7.16 (4H, m).

Workup

  1. temperatureThe solution is maintained
  2. stirringAfter stirring for 1 hour
  3. extractionis extracted with ethyl ether (3 times)
  4. washThe combined ethereal extracts are washed with aqueous sodium bicarbonate
  5. dry with materialdried over magnesium sulfate
  6. filtrationfiltered
  7. customevaporated
  8. customto give a light oil

Sources & evidence

ORD record
ord-94dacfd66d4e478984425bd4977019b9
Source dataset
uspto-grants-1991_12
Patent number
US05070207

Reaction notes

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