Isopropanol → 2-(1-Methylethoxy)-1H-isoindole-1,3(2H)-dione

HRID 1711149Notes

Reaction equation

HRID 1711149 reaction equation
[OH:1][N:2]1[C:6](=[O:7])[C:5]2=[CH:8][CH:9]=[CH:10][CH:11]=[C:4]2[C:3]1=[O:12].[C:13]1(P(C2C=CC=CC=2)C2C=CC=CC=2)[CH:18]=CC=C[CH:14]=1.CC(O)C.N(C(OCC)=O)=NC(OCC)=O>C1COCC1>[CH:13]([O:1][N:2]1[C:3](=[O:12])[C:4]2[C:5](=[CH:8][CH:9]=[CH:10][CH:11]=2)[C:6]1=[O:7])([CH3:18])[CH3:14]

Participants

6

Reactant 4

HCID 3776IsopropanolHCID 10665N-HydroxyphthalimideHCID 11776TriphenylphosphineHCID 220568ethyl N-ethoxycarbonyliminocarbamate

Product 1

HCID 27689132-(1-Methylethoxy)-1H-isoindole-1,3(2H)-dioneYield 82%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

To a suspension of N-hydroxyphthalimide (2.52 g, 15.45 mmol) in THF (60 ml) was added triphenylphosphine (4.10 g, 15.63 mmol), 2-propanol (1.2 ml, 15.67 mmol) and diethyl azodicarboxylate (2.68 ml, 17.0 mmol) and the reaction stirred overnight. The mixture was concentrated and purified by column chromatography on silica gel (Hexanes/EtOAc, 4:1) to afford 2-isopropoxy-isoindole-1,3-dione (2.59 g, 82%) as a white solid. 1H NMR (CDCl3) δ 1.38 (d, 6H, J=6 Hz), 4.52-4.58 (m, 1H), 7.73-7.76 (m, 2H), 7.83-7.85 (m, 2H).

Workup

  1. concentrationThe mixture was concentrated
  2. custompurified by column chromatography on silica gel (Hexanes/EtOAc, 4:1)

Sources & evidence

ORD record
ord-b5b570178d5e4c9a8975ddc52c4727ff
Source dataset
uspto-grants-2010_09
Patent number
US07790747B2

Reaction notes

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