Phthalimide → N-[2-[2-(trans-Styryl)oxazol-4-yl]ethyl]phthalimide

HRID 459453Notes

Reaction equation

HRID 459453 reaction equation
[C:1]1(=[O:11])[NH:5][C:4](=[O:6])[C:3]2=[CH:7][CH:8]=[CH:9][CH:10]=[C:2]12.C1(P(C2C=CC=CC=2)C2C=CC=CC=2)C=CC=CC=1.N(C(OCC)=O)=NC(OCC)=O.O[CH2:44][CH2:45][C:46]1[N:47]=[C:48](/[CH:51]=[CH:52]/[C:53]2[CH:58]=[CH:57][CH:56]=[CH:55][CH:54]=2)[O:49][CH:50]=1>O1CCCC1>[CH:51](/[C:48]1[O:49][CH:50]=[C:46]([CH2:45][CH2:44][N:5]2[C:1](=[O:11])[C:2]3=[CH:10][CH:9]=[CH:8][CH:7]=[C:3]3[C:4]2=[O:6])[N:47]=1)=[CH:52]\[C:53]1[CH:58]=[CH:57][CH:56]=[CH:55][CH:54]=1

Participants

6

Reactant 4

HCID 6809PhthalimideHCID 11776TriphenylphosphineHCID 220568ethyl N-ethoxycarbonyliminocarbamateHCID 227096224-(2-Hydroxyethyl)-2-(trans-styryl)oxazole

Product 1

HCID 22710303N-[2-[2-(trans-Styryl)oxazol-4-yl]ethyl]phthalimideYield 95.7%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

Phthalimide (200 mg), triphenylphosphine (357 mg) and diethyl azodicarboxylate (0.214 ml) were added to a solution of 4-(2-hydroxyethyl)-2-(trans-styryl)oxazole (292 mg) in tetrahydrofuran (15 ml) at room temperature, and the mixture was stirred for 4 hours. The solvent of the reaction mixture was distilled off under reduced pressure. The residue was purified by column chromatography on silica gel (hexane:ethyl acetate=3:1) to obtain the title compound (447 mg) as a colorless solid.

Workup

  1. distillationThe solvent of the reaction mixture was distilled off under reduced pressure
  2. customThe residue was purified by column chromatography on silica gel (hexane:ethyl acetate=3:1)

Sources & evidence

ORD record
ord-b72434bc57664bc69a923950bfbfe9cc
Source dataset
uspto-grants-2007_03
Patent number
US07192968B2

Reaction notes

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