Phthalimide → 2-[2-(4-Fluorophenoxy)ethyl]isoindole-1,3-dione

HRID 1895922Notes

Reaction equation

HRID 1895922 reaction equation
N(C(OCC)=O)=NC(OCC)=O.[F:13][C:14]1[CH:23]=[CH:22][C:17]([O:18][CH2:19][CH2:20]O)=[CH:16][CH:15]=1.[C:24]1(=[O:34])[C:32]2[C:27](=[CH:28][CH:29]=[CH:30][CH:31]=2)[C:26](=[O:33])[NH:25]1.C1(P(C2C=CC=CC=2)C2C=CC=CC=2)C=CC=CC=1>O1CCCC1>[F:13][C:14]1[CH:15]=[CH:16][C:17]([O:18][CH2:19][CH2:20][N:25]2[C:26](=[O:33])[C:27]3[C:32](=[CH:31][CH:30]=[CH:29][CH:28]=3)[C:24]2=[O:34])=[CH:22][CH:23]=1

Participants

6

Reactant 4

HCID 6809PhthalimideHCID 11776TriphenylphosphineHCID 220568ethyl N-ethoxycarbonyliminocarbamateHCID 5743612-(4-Fluorophenoxy)ethanol

Product 1

HCID 22303522-[2-(4-Fluorophenoxy)ethyl]isoindole-1,3-dioneYield 51.1%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

Diethyl azodicarboxylate (1.25 g, 7.20 mmol) was added to a solution of 2-(4-fluorophenoxy)ethanol (1.12 g, 7.20 mmol), isoindoline-1,3-dione (1.06 g, 7.20 mmol) and triphenylphosphine (1.89 g, 7.20 mmol) in tetrahydrofuran (20 ml) at 0° C. The reaction mixture was stirred at room temperature for 17 hours and concentrated in vacuo. The residue was purified by column chromatography (ethyl acetate/petroleum ether: 10/90 to 12.5/87.5) to give 2-(2-(4-fluorophenoxy)ethyl)isoindoline-1,3-dione (1.05 g, 51%) as a white solid: LCMS: 286 [M+1]+.

Workup

  1. concentrationconcentrated in vacuo
  2. customThe residue was purified by column chromatography (ethyl acetate/petroleum ether: 10/90 to 12.5/87.5)

Sources & evidence

ORD record
ord-a80e64b0b88f43789133a184596243b5
Source dataset
uspto-grants-2013_08
Patent number
US08518934B2

Reaction notes

Loading…