Phthalimide → 2-[3-(4-Trifluoromethylphenyl)-2-propenyl]phthalimide

HRID 856054Notes

Reaction equation

HRID 856054 reaction equation
[F:1][C:2]([F:14])([F:13])[C:3]1[CH:12]=[CH:11][C:6]([CH:7]=[CH:8][CH2:9]O)=[CH:5][CH:4]=1.[C:15]1(=[O:25])[NH:19][C:18](=[O:20])[C:17]2=[CH:21][CH:22]=[CH:23][CH:24]=[C:16]12.C1(P(C2C=CC=CC=2)C2C=CC=CC=2)C=CC=CC=1.N(C(OCC)=O)=NC(OCC)=O>C1COCC1>[F:1][C:2]([F:14])([F:13])[C:3]1[CH:12]=[CH:11][C:6]([CH:7]=[CH:8][CH2:9][C:17]23[CH:21]=[CH:22][CH:23]=[CH:24][CH:16]2[C:15]([NH:19][C:18]3=[O:20])=[O:25])=[CH:5][CH:4]=1

Participants

6

Reactant 4

HCID 6809PhthalimideHCID 11776TriphenylphosphineHCID 220568ethyl N-ethoxycarbonyliminocarbamateHCID 539257273-[4-(Trifluoromethyl)phenyl]prop-2-en-1-ol

Product 1

HCID 694807362-[3-(4-Trifluoromethylphenyl)-2-propenyl]phthalimideYield 93%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent2×

Procedure

4-(Trifluoromethyl)cinnamyl alcohol (3 g, 14.84 mmol) was dissolved in THF (60 ml), and phthalimide (2.84 g, 19.29 mmol) and triphenylphosphine (5.84 g, 22.26 mmol) were added to the solution, to which a solution of diethyl azodicarboxylate (3.87 g, 22.26 mmol) in THF (20 ml) was gradually added dropwise. The mixture was stirred at room temperature for 3 hours. The reaction mixture was concentrated under reduced pressure, and the residue was purified by silica gel column chromatography (n-hexane/methylene chloride=1/1) to afford 2-[3-(4-trifluoromethylphenyl)-2-propenyl]phthalimide (4.57 g, yield 93%) as a white powder.

Workup

  1. additionwas gradually added dropwise
  2. concentrationThe reaction mixture was concentrated under reduced pressure
  3. customthe residue was purified by silica gel column chromatography (n-hexane/methylene chloride=1/1)

Sources & evidence

ORD record
ord-938b1a119cb44be6a67436d808d3c453
Source dataset
uspto-grants-2007_08
Patent number
US07262212B2

Reaction notes

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