Acetic Anhydride → HCID 178472021, compound

HRID 251849Notes

Reaction equation

HRID 251849 reaction equation
[O:1]=[C:2]([C:9]1[CH:14]=[C:13]([F:15])[C:12]([F:16])=[C:11]([O:17][CH3:18])[C:10]=1[F:19])[CH2:3][C:4]([O:6][CH2:7][CH3:8])=[O:5].[C:20](OC(=O)C)(=O)C.[F:27][C:28]([F:32])([F:31])[CH2:29][NH2:30]>>[F:27][C:28]([F:32])([F:31])[CH2:29][NH:30][CH:20]=[C:3]([C:2](=[O:1])[C:9]1[CH:14]=[C:13]([F:15])[C:12]([F:16])=[C:11]([O:17][CH3:18])[C:10]=1[F:19])[C:4]([O:6][CH2:7][CH3:8])=[O:5]

Participants

4

Reactant 3

HCID 7918Acetic AnhydrideHCID 9773Ethanamine, 2,2,2-trifluoro-HCID 10588473Ethyl 3-oxo-3-(2,4,5-trifluoro-3-methoxyphenyl)propanoate

Product 1

HCID 178472021HCID 178472021, compound

Procedure

2.00 g (5.79 mmol) of ethyl 3-oxo-3-(2,4,5-trifluoro-3-methoxyphenyl)propanoate are stirred in 3.8 ml (4.14 g, 40.55 mmol) of acetic anhydride and 4.82 ml (4.29 g, 28.96 mmol) of thriethylorthoformate for 2 h under reflux. The solvent is then completely removed on a rotary evaporator and the residue is dissolved in 10 ml of ethanol. 1.03 g (10.43 mmol) of 2,2,2-trifluoro-1-aminoethane are added dropwise to the ice cold solution, the mixture is brought to room temperature and stirred over night at this temperature. For the work-up the solvent is removed and the residue is reacted further as a crude product without purification steps.

Workup

  1. temperature4.82 ml (4.29 g, 28.96 mmol) of thriethylorthoformate for 2 h under reflux
  2. customThe solvent is then completely removed on a rotary evaporator
  3. dissolutionthe residue is dissolved in 10 ml of ethanol
  4. customis brought to room temperature
  5. customFor the work-up the solvent is removed
  6. customthe residue is reacted further as a crude product without purification steps

Sources & evidence

ORD record
ord-f482614a751d45a1aaf5912e8e79f3b3
Source dataset
uspto-grants-2011_01
Patent number
US07867992B2

Reaction notes

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