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

HRID 1917914Notes

Reaction equation

HRID 1917914 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-188c1471ce8a4fc19a2aa70cc6a03d64
Source dataset
uspto-grants-2013_12
Patent number
US08618289B2

Reaction notes

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