2,2,6-Trimethyl-4H-1,3-dioxin-4-one → 3-(3-Acetoacetoxypropyl)-5-(4-chlorophenyl)-1-(4-methoxyphenyl) pyrazole

HRID 373492Notes

Reaction equation

HRID 373492 reaction equation
[Cl:1][C:2]1[CH:7]=[CH:6][C:5]([C:8]2[N:12]([C:13]3[CH:18]=[CH:17][C:16]([O:19][CH3:20])=[CH:15][CH:14]=3)[N:11]=[C:10]([CH2:21][CH2:22][CH2:23][OH:24])[CH:9]=2)=[CH:4][CH:3]=1.[CH3:25][C:26]1[O:32]C(C)(C)O[C:28](=[O:29])[CH:27]=1>>[C:28]([O:24][CH2:23][CH2:22][CH2:21][C:10]1[CH:9]=[C:8]([C:5]2[CH:4]=[CH:3][C:2]([Cl:1])=[CH:7][CH:6]=2)[N:12]([C:13]2[CH:18]=[CH:17][C:16]([O:19][CH3:20])=[CH:15][CH:14]=2)[N:11]=1)(=[O:29])[CH2:27][C:26]([CH3:25])=[O:32]

Participants

3

Reactant 2

HCID 793682,2,6-Trimethyl-4H-1,3-dioxin-4-oneHCID 14497416HCID 14497416, compound

Product 1

HCID 179135833-(3-Acetoacetoxypropyl)-5-(4-chlorophenyl)-1-(4-methoxyphenyl) pyrazoleYield 80%

Procedure

5-(4-Chlorophenyl)-3-(3-hydroxypropyl)-1-(4-methoxyphenyl) pyrazole (1.71 g, 0.005 moles) and 2,2,6-trimethyl-1,3-dioxen-4-one (0.71 g, 0.005 moles) were dissolved in 100 ml of xylenes. The solution was stirred under reflux for 16 hours. At that time, the solution was cooled to room temperature, and concentrated in vacuo to a yellow oil. The oil was flash chromatographed on silica gel to afford 59 (1.7 g, 80%) as a pale yellow oil.

Workup

  1. temperatureunder reflux for 16 hours
  2. concentrationconcentrated in vacuo to a yellow oil
  3. customchromatographed on silica gel

Sources & evidence

ORD record
ord-be504d02f99a4905adaeb22a4e27c7e3
Source dataset
uspto-grants-1992_11
Patent number
US05164381

Reaction notes

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