tert-Butyl 3-aminocrotonate → HCID 18962946, compound

HRID 1707278Notes

Reaction equation

HRID 1707278 reaction equation
[Cl:1][C:2]1[C:7]([Cl:8])=[CH:6][CH:5]=[CH:4][C:3]=1[CH:9]=[C:10]([C:18](=[O:20])[CH3:19])[C:11](=O)[CH2:12][CH2:13][CH2:14][CH2:15][Cl:16].[NH2:21]/[C:22](/[CH3:31])=[CH:23]\[C:24]([O:26][C:27]([CH3:30])([CH3:29])[CH3:28])=[O:25]>C(O)CCC>[C:18]([C:10]1[CH:9]([C:3]2[CH:4]=[CH:5][CH:6]=[C:7]([Cl:8])[C:2]=2[Cl:1])[C:23]([C:24]([O:26][C:27]([CH3:30])([CH3:29])[CH3:28])=[O:25])=[C:22]([CH3:31])[NH:21][C:11]=1[CH2:12][CH2:13][CH2:14][CH2:15][Cl:16])(=[O:20])[CH3:19]

Participants

4

Reactant 2

HCID 12221517tert-Butyl 3-aminocrotonateHCID 542578438-Chloro-3-[(2,3-dichlorophenyl)methylidene]octane-2,4-dione

Product 1

HCID 18962946HCID 18962946, compound

Reagents, catalysts & solvents 1

HCID 2631-ButanolSolvent

Procedure

25 g (70 mmol) 6-(2,3-dichlorophenyl-methylene)-1-chloro-5,7-octanedione and 22 g (0.14 mol) tert-butyl β-amino-crotonate are boiled under reflux in 200 ml 1-butanol for 6 h. The mixture is concentrated and the residue is prepurified by chromatography with toluene/acetone=8/2. The product thus obtained is chromatographed again over silica gel with toluene/acetone=99/1. The title compound is obtained as a yellow oil. Yield: 5.8 g (18%).

Workup

  1. concentrationThe mixture is concentrated
  2. customThe product thus obtained
  3. customis chromatographed again over silica gel with toluene/acetone=99/1

Sources & evidence

ORD record
ord-6338a497ca4b481481c47ffc06471a26
Source dataset
uspto-grants-1994_10
Patent number
US05352684

Reaction notes

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