Phthalimide → 2-(1-Methylbut-3-ynyl)isoindole-1,3-dione

HRID 2041867Notes

Reaction equation

HRID 2041867 reaction equation
[CH3:1][CH:2](O)[CH2:3][C:4]#[CH:5].[C:7]1(=[O:17])[NH:11][C:10](=[O:12])[C:9]2=[CH:13][CH:14]=[CH:15][CH:16]=[C:8]12.C1(P(C2C=CC=CC=2)C2C=CC=CC=2)C=CC=CC=1.N(C(OCC)=O)=NC(OCC)=O>O1CCCC1>[CH3:5][CH:4]([N:11]1[C:7](=[O:17])[C:8]2[C:9](=[CH:13][CH:14]=[CH:15][CH:16]=2)[C:10]1=[O:12])[CH2:3][C:2]#[CH:1]

Participants

6

Reactant 4

HCID 6809PhthalimideHCID 11776TriphenylphosphineHCID 929154-Pentyn-2-olHCID 220568ethyl N-ethoxycarbonyliminocarbamate

Product 1

HCID 113333492-(1-Methylbut-3-ynyl)isoindole-1,3-dioneYield 17.4%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

400 ml of dry tetrahydrofuran, 5.00 g of 4-pentin-2-ol, 9.65 g of phthalimide, and 17.13 g of triphenylphosphine were added to a nitrogen-substituted flask. Thereafter, 30 ml of diethyl azodicarboxylate (40% toluene solution) was slowly added dropwise to the obtained solution at a room temperature, and the obtained mixture was then stirred at a room temperature for 1 day. Thereafter, the reaction solution was concentrated, and 300 ml of water was then added to the residue, followed by extraction with 250 ml of ethyl acetate twice. The organic layer was washed with 200 ml of water and then with 200 ml of a saturated brine. The resultant was dried over magnesium sulfate. The magnesium sulfate was filtrated, and the organic layer was then concentrated. The residue was then purified by column chromatography (Wako Gel C-200; toluene), so as to obtain 2.20 g of a phthalimide compound.

Workup

  1. concentrationThereafter, the reaction solution was concentrated
  2. addition300 ml of water was then added to the residue
  3. extractionfollowed by extraction with 250 ml of ethyl acetate twice
  4. washThe organic layer was washed with 200 ml of water
  5. dry with materialThe resultant was dried over magnesium sulfate
  6. filtrationThe magnesium sulfate was filtrated
  7. concentrationthe organic layer was then concentrated
  8. customThe residue was then purified by column chromatography (Wako Gel C-200; toluene)

Sources & evidence

ORD record
ord-4317b675cdb74ec996bf5a6c983c4735
Source dataset
uspto-grants-2013_11
Patent number
US08586505B2

Reaction notes

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