Allyl Alcohol → Allyl 2-[5-(2,4-dimethylbenzoyl)-1-methylpyrrol-2-yl)-2-(2-fluoro-4-nitrophenyl)-acetate

HRID 618321Notes

Reaction equation

HRID 618321 reaction equation
[CH3:1][C:2]1[CH:30]=[C:29]([CH3:31])[CH:28]=[CH:27][C:3]=1[C:4]([C:6]1[N:10]([CH3:11])[C:9]([CH:12]([C:17]2[CH:22]=[CH:21][C:20]([N+:23]([O-:25])=[O:24])=[CH:19][C:18]=2[F:26])[C:13]([O:15][CH3:16])=[O:14])=[CH:8][CH:7]=1)=[O:5].[CH2:32](O)[CH:33]=C>CC(C)[O-].CC(C)[O-].CC(C)[O-].CC(C)[O-].[Ti+4]>[CH3:1][C:2]1[CH:30]=[C:29]([CH3:31])[CH:28]=[CH:27][C:3]=1[C:4]([C:6]1[N:10]([CH3:11])[C:9]([CH:12]([C:17]2[CH:22]=[CH:21][C:20]([N+:23]([O-:25])=[O:24])=[CH:19][C:18]=2[F:26])[C:13]([O:15][CH2:16][CH:32]=[CH2:33])=[O:14])=[CH:8][CH:7]=1)=[O:5]

Participants

4

Reactant 2

HCID 7858Allyl AlcoholHCID 23285816Methyl 2-[5-(2,4-dimethylbenzoyl)-1-methylpyrrol-2-yl)-2-(2-fluoro-4-nitrophenyl)acetate

Product 1

HCID 23285845Allyl 2-[5-(2,4-dimethylbenzoyl)-1-methylpyrrol-2-yl)-2-(2-fluoro-4-nitrophenyl)-acetateYield 97%

Reagents, catalysts & solvents 1

HCID 11026Titanium isopropoxideCatalyst

Procedure

To a solution of methyl 2-[5- (2,4-dimethylbenzoyl)-1-methylpyrrol-2-yl)-2-(2-fluoro-4-nitrophenyl)acetate (3.51 g, 8.27 mmol) [prepared as described in Example 6, Step(c)] in 75 ml allyl alcohol was added titanium tetraisopropoxide (0.244 ml, 0.827 mmol), and the reaction mixture was heated to reflux. After 36 h, the reaction mixture was cooled to room temperature, and partitioned between ether and water. The organic layer was separated, dried over magnesium sulfate, and concentrated to dryness to give allyl 2-[5-(2,4-dimethylbenzoyl)-1-methylpyrrol-2-yl)-2-(2-fluoro-4-nitrophenyl)-acetate (3.60 g, 97%) as a pale yellow oil. ##STR36##

Workup

  1. temperaturethe reaction mixture was heated to reflux
  2. custompartitioned between ether and water
  3. customThe organic layer was separated
  4. dry with materialdried over magnesium sulfate
  5. concentrationconcentrated to dryness

Sources & evidence

ORD record
ord-8c8336e147c54f87a3f9fb6ef375f633
Source dataset
uspto-grants-1999_09
Patent number
US05952368

Reaction notes

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