Phthalimide → HCID 359215, compound

HRID 2229290Notes

Reaction equation

HRID 2229290 reaction equation
[OH:1][CH2:2][C:3]#[C:4][CH2:5]O.C1(P(C2C=CC=CC=2)C2C=CC=CC=2)C=CC=CC=1.[C:26]1(=[O:36])[NH:30][C:29](=[O:31])[C:28]2=[CH:32][CH:33]=[CH:34][CH:35]=[C:27]12.N(C(OC(C)C)=O)=NC(OC(C)C)=O>C1COCC1>[OH:1][CH2:2][C:3]#[C:4][CH2:5][N:30]1[C:26](=[O:36])[C:27]2=[CH:35][CH:34]=[CH:33][CH:32]=[C:28]2[C:29]1=[O:31]

Participants

6

Reactant 4

HCID 6809PhthalimideHCID 80662-Butyne-1,4-diolHCID 11776TriphenylphosphineHCID 75555Diisopropyl diazene-1,2-dicarboxylate

Product 1

HCID 359215HCID 359215, compoundYield 53%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

1,4-Dihydroxy-2-butyne (430 mg, 5.0 mmol), triphenylphosphine (1.44 g, 5.5 mmol) and phthalimide (1.47 g, 10.0 mmol) were dissolved in 50 mL of dry THF. To this solution, with stirring under dry argon, was added diisopropyl azodicarboxylate (1.09 mL, 5.25 mmol) dropwise. After stirring at room temperature for 6 hours, the reaction mixture was evaporated in vacuo to remove the THF. The residue was dissolved in methylene chloride (25 mL) and ethyl acetate (25 mL), the insoluble phthalimide was filtered off and the filtrate was concentrated in vacuo. The residue was subjected to flash column chromatography (eluent, ethyl acetate-hexane, 1:1) to give 1-hydroxy-4-phthalimido-2-butyne (240) as a white solid (570 mg, 53%). 1H NMR (CDCl3) δ7.88 (2H, dd, J=5.7, 3.1 Hz), 7.74 (2H, dd, J 5.7, 3.1 Hz), 4.49 (2H, t, J=2.0 Hz), 4.24 (2H, dt, J=6.2, 2.0 Hz), 1.92 (1 H, t, J=6.2 Hz).

Workup

  1. stirringAfter stirring at room temperature for 6 hours
  2. customthe reaction mixture was evaporated in vacuo
  3. customto remove the THF
  4. dissolutionThe residue was dissolved in methylene chloride (25 mL)
  5. filtrationethyl acetate (25 mL), the insoluble phthalimide was filtered off
  6. concentrationthe filtrate was concentrated in vacuo

Sources & evidence

ORD record
ord-6263c9e2dac94405a6c5ac3b62e94445
Source dataset
uspto-grants-2002_07
Patent number
US06420392B1

Reaction notes

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