Phthalimide → HCID 359215, compound

HRID 546083Notes

Reaction equation

HRID 546083 reaction equation
[CH2:1](O)[C:2]#[C:3][CH2:4][OH: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(OC(C)C)=O)=NC(OC(C)C)=O>O1CCCC1>[OH:5][CH2:4][C:3]#[C:2][CH2:1][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]

Participants

6

Reactant 4

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

Product 1

HCID 359215HCID 359215, compoundYield 39%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Conditions

Temperature
0 °C

Procedure

But-2-yne-1,4-diol (8.78 g, 102 mmol), phthalimide (5.00 g, 33.98 mmol) and triphenylphosphine (8.91 g, 33.98 mmol) were combined and dissolved in tetrahydrofuran (165 mL) and then chilled to 0° C. While stirring, diisopropyl azodicarboxylate (10 mL, 50.97 mmol) was added dropwise. The ice bath was removed and the reaction continued to stir at 25° C. for 16 h. The reaction was concentrated in vacuo to give a thick golden oil. Purification by flash column chromatography (Merck silica gel 60, 40-63 μm; 10% ethyl acetate/hexanes to 50% ethyl acetate/hexanes) afforded 2-(4-hydroxy-but-2-ynyl)-isoindole-1,3-dione (2.83 g, 39%) as a white powder: ESI-LRMS m/e calcd for C12H9NO3 [M+] 215.1, found 216.3 [M+H+], 431.6 [2M+H+].

Workup

  1. customThe ice bath was removed
  2. stirringto stir at 25° C. for 16 h
  3. concentrationThe reaction was concentrated in vacuo
  4. customto give a thick golden oil
  5. customPurification by flash column chromatography (Merck silica gel 60, 40-63 μm; 10% ethyl acetate/hexanes to 50% ethyl acetate/hexanes)

Sources & evidence

ORD record
ord-442c4f8ff394478097f999ca082fcbfc
Source dataset
uspto-grants-2011_05
Patent number
US07935699B2

Reaction notes

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