Phthalimide → HCID 90051757, compound

HRID 2284719Notes

Reaction equation

HRID 2284719 reaction equation
[CH3:1][C:2]([CH3:8])([C:6]#[CH:7])[CH2:3][CH2:4]O.C1(P(C2C=CC=CC=2)C2C=CC=CC=2)C=CC=CC=1.[C:28]1(=[O:38])[NH:32][C:31](=[O:33])[C:30]2=[CH:34][CH:35]=[CH:36][CH:37]=[C:29]12.N(C(OCC)=O)=NC(OCC)=O>O1CCCC1.C1(C)C=CC=CC=1.C(OCC)(=O)C.O>[CH3:1][C:2]([CH3:8])([C:3]#[CH:4])[CH2:6][CH2:7][N:32]1[C:28](=[O:38])[C:29]2[C:30](=[CH:34][CH:35]=[CH:36][CH:37]=2)[C:31]1=[O:33]

Participants

9

Reactant 4

HCID 6809PhthalimideHCID 11776TriphenylphosphineHCID 220568ethyl N-ethoxycarbonyliminocarbamateHCID 102407894-Pentyn-1-ol, 3,3-dimethyl-

Product 1

HCID 90051757HCID 90051757, compoundYield 52.4%

Reagents, catalysts & solvents 4

HCID 962WaterSolventHCID 1140TolueneSolventHCID 8028TetrahydrofuranSolventHCID 8857Ethyl AcetateSolvent

Procedure

To a solution of 3,3-dimethyl-4-pentyn-1-ol (6.3 g) synthesized according to the method described in Chemistry A European Journal, 2005, 11, pp. 308-320, triphenylphosphine (29.4 g), and phthalimide (16.5 g) in tetrahydrofuran (200 mL), a 2.2 mol/L solution of diethyl azodicarboxylate in toluene (51 mL) was added dropwise under ice cooling, and the mixture was stirred at the same temperature. To the reaction mixture, water and ethyl acetate were added. The organic layer was separated, washed successively with water and saturated aqueous sodium chloride, and then dried over anhydrous sodium sulfate, and the solvent was evaporated under reduced pressure. To the obtained residue, ethyl acetate were added, the insoluble matter was removed by filtration, and then the solvent was evaporated under reduced pressure. The obtained residue was purified by silica gel column chromatography to obtain 2-(3,3-dimethyl-4-pentyn-1-yl)isoindoline-1,3-dione (F12, 7.1 g) as pale yellow solid.

Workup

  1. customThe organic layer was separated
  2. washwashed successively with water and saturated aqueous sodium chloride
  3. dry with materialdried over anhydrous sodium sulfate
  4. customthe solvent was evaporated under reduced pressure
  5. additionTo the obtained residue, ethyl acetate were added
  6. customthe insoluble matter was removed by filtration
  7. customthe solvent was evaporated under reduced pressure
  8. customThe obtained residue was purified by silica gel column chromatography

Sources & evidence

ORD record
ord-e3b60c050efc42f4884ef62a88eb8e1f
Source dataset
uspto-grants-2015_09
Patent number
US09145415B2

Reaction notes

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