Phthalimide → 2-[4-(4-Chlorophenyl)but-3-yn-2-yl]-1H-isoindole-1,3(2H)-dione

HRID 597885Notes

Reaction equation

HRID 597885 reaction equation
[Cl:1][C:2]1[CH:7]=[CH:6][C:5]([C:8]#[C:9][CH:10](O)[CH3:11])=[CH:4][CH:3]=1.[C:13]1(=[O:23])[NH:17][C:16](=[O:18])[C:15]2=[CH:19][CH:20]=[CH:21][CH:22]=[C:14]12.C1C=CC(P(C2C=CC=CC=2)C2C=CC=CC=2)=CC=1.CCOC(/N=N/C(OCC)=O)=O>C1COCC1>[Cl:1][C:2]1[CH:7]=[CH:6][C:5]([C:8]#[C:9][CH:10]([N:17]2[C:13](=[O:23])[C:14]3[C:15](=[CH:19][CH:20]=[CH:21][CH:22]=3)[C:16]2=[O:18])[CH3:11])=[CH:4][CH:3]=1

Participants

6

Reactant 4

HCID 6809PhthalimideHCID 11776TriphenylphosphineHCID 5462977Diethyl azodicarboxylateHCID 23006387HCID 23006387, compound

Product 1

HCID 573568212-[4-(4-Chlorophenyl)but-3-yn-2-yl]-1H-isoindole-1,3(2H)-dioneYield 79.7%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

To a solution of 4-(4-chloro-phenyl)-but-3-yn-2-ol (3 g, 16.6 mmol), phthalimide (3.7 g, 25.2 mmol, 1.5 eq.) and PPh3 (4.8 g, 18.3 mmol, 1.1 eq.) in 100 mL of THF cooled to 0° C. with an ice bath was added dropwise DEAD (i.e., diethyl azodicarboxylate) (3.1 mL, 19.9 mmol, 1.2 eq.). The ice-bath was removed and the mixture was stirred overnight at room temperature. The THF was evaporated and the residue was stirred with 200 mL of 1:1 ether-hexane mixture for 1 hr. The precipitate was filtered off and the filtrate was concentrated and chromatographed with 15% ethyl acetate-hexane to provide 4.1 g of 2-[3-(4-chloro-phenyl)-1-methyl-prop-2-ynyl]-isoindole-1,3-dione.

Workup

  1. customThe ice-bath was removed
  2. customThe THF was evaporated
  3. stirringthe residue was stirred with 200 mL of 1:1 ether-hexane mixture for 1 hr
  4. filtrationThe precipitate was filtered off
  5. concentrationthe filtrate was concentrated
  6. customchromatographed with 15% ethyl acetate-hexane

Sources & evidence

ORD record
ord-5f1d808e0cbc4d379ae7eb43841a6fee
Source dataset
uspto-grants-2011_03
Patent number
US07897601B2

Reaction notes

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