N-Hydroxyphthalimide → HCID 19789717, compound

HRID 1655930Notes

Reaction equation

HRID 1655930 reaction equation
[CH3:1][O:2][CH2:3][O:4][CH2:5][CH2:6][CH2:7][OH:8].C1(P(C2C=CC=CC=2)C2C=CC=CC=2)C=CC=CC=1.O[N:29]1[C:33](=[O:34])[C:32]2=[CH:35][CH:36]=[CH:37][CH:38]=[C:31]2[C:30]1=[O:39].N(C(OCC)=O)=NC(OCC)=O>O1CCCC1>[CH3:1][O:2][CH2:3][O:4][CH2:5][CH2:6][CH2:7][O:8][N:29]1[C:30](=[O:39])[C:31]2=[CH:38][CH:37]=[CH:36][CH:35]=[C:32]2[C:33]1=[O:34]

Participants

6

Reactant 4

HCID 10665N-HydroxyphthalimideHCID 11776TriphenylphosphineHCID 220568ethyl N-ethoxycarbonyliminocarbamateHCID 19789718HCID 19789718, compound

Product 1

HCID 19789717HCID 19789717, compoundYield 41%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent2×

Procedure

A solution of 3-(methoxymethoxy)propanol (5 g, 41.6 mmol), triphenylphosphine (13.1 g, 50 mmol) and N-hydroxyphthalimide (7.25 g, 44 mmol) in dry tetrahydrofuran (150 ml) was cooled to 0°-5° C. and treated with diethyl azodicarboxylate (8.7 g, 50 mmol) in dry tetrahydrofuran (10 ml) over 1/2 hr. The reaction was then stirred at ambient temperature for 18 hr. The solvent was removed in vacuo and the residue was dissolved in diethyl ether (100 ml) and the mixture cooled to 0°-5° C. for 3 hr. The solid was removed by filtration and the filtrate was evaporated in vacuo. The residue was purified by column chromatography on silica eluting with hexane:ethyl acetate (70:30) to give the title compound as an oil (4.5 g, 41%). νmax (Film) 2960, 2900, 1800, 1740, 1620, 1480 and 1380 cm-1 ; δH (CDCl3) 2.07 (2H, quintet, J=6.3 Hz, CH2CH2CH2), 3.38 (3H, s, OCH3), 3.77 (2H, t, J=6.3 Hz, CH2OCH2OCH3), 4.33 (2H, t, J=6.3 Hz, CH2ON), 4.66 (2H, s, OCH2O), 7.83 (4H, m, ArH).

Workup

  1. customThe solvent was removed in vacuo
  2. dissolutionthe residue was dissolved in diethyl ether (100 ml)
  3. temperaturethe mixture cooled to 0°-5° C. for 3 hr
  4. customThe solid was removed by filtration
  5. customthe filtrate was evaporated in vacuo
  6. customThe residue was purified by column chromatography on silica eluting with hexane:ethyl acetate (70:30)

Sources & evidence

ORD record
ord-d37f754f78ec4e5f945f649a87a8df13
Source dataset
uspto-grants-1993_10
Patent number
US05252575

Reaction notes

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