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

HRID 369386Notes

Reaction equation

HRID 369386 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-b74fe0bbc5b44a1399f8857de0b22743
Source dataset
uspto-grants-2000_10
Patent number
US06136844

Reaction notes

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