Phthalimide → 2-(BUT-3-YN-2-YL)ISOINDOLINE-1,3-DIONE

HRID 404867Notes

Reaction equation

HRID 404867 reaction equation
[CH3:1][CH:2](O)[C:3]#[CH:4].[C:6]1(=[O:16])[NH:10][C:9](=[O:11])[C:8]2=[CH:12][CH:13]=[CH:14][CH:15]=[C:7]12.C1(P(C2C=CC=CC=2)C2C=CC=CC=2)C=CC=CC=1.N(C(OCC)=O)=NC(OCC)=O>O1CCCC1>[CH3:4][CH:3]([N:10]1[C:6](=[O:16])[C:7]2[C:8](=[CH:12][CH:13]=[CH:14][CH:15]=2)[C:9]1=[O:11])[C:2]#[CH:1]

Participants

6

Reactant 4

HCID 6809PhthalimideHCID 11776TriphenylphosphineHCID 162393-Butyn-2-olHCID 220568ethyl N-ethoxycarbonyliminocarbamate

Product 1

HCID 6036332-(BUT-3-YN-2-YL)ISOINDOLINE-1,3-DIONEYield 63.4%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

To a solution of but-3-yn-2-ol (13.3 g, 0.19 mol), phthalimide (28.5 g, 0.19 mol) and triphenylphosphine (76.0 g, 0.28 mol) in tetrahydrofuran was added diethyl azodicarboxylate (123.8 g, 0.28 mol, 310 mL of 40% toluene solution) drop wise at room temperature. The reaction mixture was stirred for 16 h. Solvent was removed and the residue was treated with 600 mL mixture of ether and hexane (1:1). The precipitate was filtered off and the filtrate was concentrated to give 90 g of the crude. The crude was then purified on silica gel eluting with 15% ethyl acetate in hexane to give 24 g of the title compound as a white solid (63% yield), 1H NMR (300 MHz, CDCl3) δ ppm 1.72 (d, J=6.99 Hz, 3H) 2.35 (d, J=2.21 Hz, 1H) 5.22 (dt, J=14.34, 7.35, 2.57 Hz, 1H) 7.68-7.78 (m, 2H) 7.82-7.90 (m, 2H), MS (ESI), M/Z: 200.0 (M+H)+.

Workup

  1. customSolvent was removed
  2. additionthe residue was treated with 600 mL mixture of ether and hexane (1:1)
  3. filtrationThe precipitate was filtered off
  4. concentrationthe filtrate was concentrated
  5. customto give 90 g of the crude
  6. customThe crude was then purified on silica gel eluting with 15% ethyl acetate in hexane

Sources & evidence

ORD record
ord-fffff6fd3d124a66a99fbe23513a5473
Source dataset
uspto-grants-2014_06
Patent number
US08748627B2

Reaction notes

Loading…