Ammonium Hydroxide → 4-Amino-4-ethoxy-1,1,1-trifluorobut-3-en-2-one

HRID 871513Notes

Reaction equation

HRID 871513 reaction equation
[CH2:1]([O:3][C:4](OCC)=[CH:5][C:6](=[O:11])[C:7]([F:10])([F:9])[F:8])[CH3:2].[NH4+:15].[OH-]>CC#N.O>[NH2:15]/[C:4](/[O:3][CH2:1][CH3:2])=[CH:5]\[C:6](=[O:11])[C:7]([F:10])([F:9])[F:8]

Participants

5

Reactant 2

HCID 14923Ammonium HydroxideHCID 108999144,4-Diethoxy-1,1,1-trifluorobut-3-en-2-one

Product 1

HCID 151117544-Amino-4-ethoxy-1,1,1-trifluorobut-3-en-2-oneYield 93%

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 6342AcetonitrileSolvent

Procedure

To a solution of 4,4-diethoxy-1,1,1-trifluorobut-3-en-2-one (7.94 g, 37.4 mmol) in MeCN (30 mL) at room temperature was dropped 28% solution of NH4OH in water (7 mL). It was stirred at room temperature overnight. After solvent was removed under reduced pressure, to it was added CH2Cl2 and washed with water. The organic layer was dried over MgSO4 and concentrated under reduced pressure to afford (E)-4-amino-4-ethoxy-1,1,1-trifluorobut-3-en-2-one as solid (6.371 g, 93%). 1H NMR (300 MHz, CDCl3) δ 9.79 (br, 1H), 5.66 br, 1H), 5.13 (s, 1H), 4.15 (q, 2H), 1.38 (t, 3H); LC-MS (ESI) m/z 184 (M+H)+.

Workup

  1. customAfter solvent was removed under reduced pressure, to it
  2. additionwas added CH2Cl2
  3. washwashed with water
  4. dry with materialThe organic layer was dried over MgSO4
  5. concentrationconcentrated under reduced pressure

Sources & evidence

ORD record
ord-a7ccf7d97d914400b538378055e9937a
Source dataset
uspto-grants-2015_03
Patent number
US08969587B2

Reaction notes

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