Phthalimide → HCID 69673484, compound

HRID 2041878Notes

Reaction equation

HRID 2041878 reaction equation
[CH:1]([CH:3]([C:6]#[C:7][C:8]1[CH:13]=[CH:12][CH:11]=[CH:10][CH:9]=1)[CH2:4]O)=[CH2:2].[C:14]1(=[O:24])[NH:18][C:17](=[O:19])[C:16]2=[CH:20][CH:21]=[CH:22][CH:23]=[C:15]12.C1(P(C2C=CC=CC=2)C2C=CC=CC=2)C=CC=CC=1.N(C(OCC)=O)=NC(OCC)=O>C1(C)C=CC=CC=1>[CH:1]([CH:3]([C:6]#[C:7][C:8]1[CH:13]=[CH:12][CH:11]=[CH:10][CH:9]=1)[CH2:4][N:18]1[C:14](=[O:24])[C:15]2[C:16](=[CH:20][CH:21]=[CH:22][CH:23]=2)[C:17]1=[O:19])=[CH2:2]

Participants

6

Reactant 4

HCID 6809PhthalimideHCID 11776TriphenylphosphineHCID 220568ethyl N-ethoxycarbonyliminocarbamateHCID 14140997HCID 14140997, compound

Product 1

HCID 69673484HCID 69673484, compoundYield 31.8%

Reagents, catalysts & solvents 1

HCID 1140TolueneSolvent

Procedure

55 ml of toluene, 1.80 g of 2-vinyl-4-phenyl-3-butyn-ol, 1.93 g of phthalimide, and 3.45 g of triphenylphosphine were added to a nitrogen-substituted flask. Then, 5.30 g of diethyl azodicarboxylate (40% toluene solution) was slowly added dropwise to the above obtained solution under cooling on ice. The temperature was increased to a room temperature, and the obtained mixture was then stirred for 1 day. Thereafter, the reaction solution was concentrated, and 200 ml of diethyl ether was then added to the residue. The appearing solid was removed by filtration. The residue was concentrated, and it was then purified by flash chromatography (manufactured by Biotage AB; Isolera™), so as to obtain 1.00 g of 2-(2-vinyl-4-phenyl-3-butynyl)isoindol-1,3-dione.

Workup

  1. temperatureunder cooling on ice
  2. concentrationThereafter, the reaction solution was concentrated
  3. addition200 ml of diethyl ether was then added to the residue
  4. customThe appearing solid was removed by filtration
  5. concentrationThe residue was concentrated
  6. customit was then purified by flash chromatography (manufactured by Biotage AB; Isolera™)

Sources & evidence

ORD record
ord-5fefa85ccdee4864b613868ec53bbbda
Source dataset
uspto-grants-2013_11
Patent number
US08586505B2

Reaction notes

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