1-(4-Chlorophenyl)-4,4,4-trifluorobutane-1,3-dione → HCID 59487337, compound

HRID 1099591Notes

Reaction equation

HRID 1099591 reaction equation
[Cl:1][C:2]1[CH:7]=[CH:6][C:5]([C:8](=O)[CH2:9][C:10](=O)[C:11]([F:14])([F:13])[F:12])=[CH:4][CH:3]=1.[NH2:17][C:18]([CH:24]([CH3:26])[CH3:25])=[CH:19][C:20]([O:22][CH3:23])=[O:21]>C(#N)C>[Cl:1][C:2]1[CH:7]=[CH:6][C:5]([C:8]2[CH:9]=[C:10]([C:11]([F:14])([F:13])[F:12])[C:19]([C:20]([O:22][CH3:23])=[O:21])=[C:18]([CH:24]([CH3:26])[CH3:25])[N:17]=2)=[CH:4][CH:3]=1

Participants

4

Reactant 2

HCID 27738321-(4-Chlorophenyl)-4,4,4-trifluorobutane-1,3-dioneHCID 70700467Methyl 3-amino-4-methylpent-2-enoate

Product 1

HCID 59487337HCID 59487337, compound

Reagents, catalysts & solvents 1

HCID 6342AcetonitrileSolvent

Procedure

150 mg (0.599 mmol) of 1-(4-chlorophenyl)-4,4,4-trifluorobutane-1,3-dione [Katsuyama et al., Synthesis, 1321-1324 (1997)] and 171 mg (1.20 mmol) of methyl 3-amino-4-methylpent-2-enoate [Holz et al., J. Org. Chem. 68., 1701-1707 (2003)] in 2 ml of acetonitrile were reacted at reflux temperature overnight. The volatile components were then removed on a rotary evaporator. The residue was purified by preparative HPLC (mobile phase: acetonitrile/water, gradient 10:90→90:10). This gave 34 mg (16% of theory) of the target compound.

Workup

  1. temperatureat reflux temperature overnight
  2. customThe volatile components were then removed on a rotary evaporator
  3. customThe residue was purified by preparative HPLC (mobile phase: acetonitrile/water, gradient 10:90→90:10)

Sources & evidence

ORD record
ord-db48fd3648654dc6ac969c8d9ead8d8d
Source dataset
uspto-grants-2012_03
Patent number
US08143411B2

Reaction notes

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