N-Hydroxyphthalimide → HCID 19789733, compound

HRID 1655929Notes

Reaction equation

HRID 1655929 reaction equation
[CH:1]([O:4][CH2:5][O:6][CH2:7][CH2:8][CH2:9][OH:10])([CH3:3])[CH3:2].O[N:12]1[C:16](=[O:17])[C:15]2=[CH:18][CH:19]=[CH:20][CH:21]=[C:14]2[C:13]1=[O:22].C1(P(C2C=CC=CC=2)C2C=CC=CC=2)C=CC=CC=1.N(C(OCC)=O)=NC(OCC)=O>O1CCCC1>[CH:1]([O:4][CH2:5][O:6][CH2:7][CH2:8][CH2:9][O:10][N:12]1[C:13](=[O:22])[C:14]2=[CH:21][CH:20]=[CH:19][CH:18]=[C:15]2[C:16]1=[O:17])([CH3:3])[CH3:2]

Participants

6

Reactant 4

HCID 10665N-HydroxyphthalimideHCID 11776TriphenylphosphineHCID 220568ethyl N-ethoxycarbonyliminocarbamateHCID 19789726HCID 19789726, compound

Product 1

HCID 19789733HCID 19789733, compoundYield 88.6%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent2×

Procedure

A mixture of [3-(isopropoxymethoxy)propanol (5.3 g, 35.8 mmol), N-hydroxyphthalimide (5.83 g, 35.8 mmol) and triphenylphosphine (10.48 g, 40 mmol) in dry tetrahydrofuran (75 ml) at 0°-5° C.; was treated with a solution of diethyl azodicarboxylate (6.96 g, 40 mmol) in dry tetrahydrofuran (15 ml) over 15 min. The reaction mixture was stirred at ambient temperature for 18 hr. The solvent was removed in vacuo and the residue was dissolved in diethyl ether (100 ml) and cooled to 5° C. for 2 hr. The solid was filtered off, the filtrate evaporated in vacuo, and the residue purified by column chromatography on silica eluting with hexane:ethyl acetate (70:30) to give the title compound as an oil (9.3 g, 88%). νmax (Film) 2980, 2940, 2900, 1740, 1475 and 1380 cm-1 ; δH (CDCl3) 1.17 (3H, s, CH3), 1.19 (3H, s, CH3), 2.06 (2H, quintet, J=6.3 Hz CH2CH2CH2), 3.77 (2H, t, J=6.3 Hz, CH2OCH2OCH(CH3)2), 3.88 (1H, septet, J=6.3 Hz, OCH(CH3)2), 4.32 (2H, t, J=6.3 Hz CH2ON), 4.73 (2H, s, OCH2O), 7.78 (4H, m, ArH). (Found: C, 16.53; H, 6.59; N, 4.71%: C15H19NO5 requires: C, 16.42; H, 6.52; N, 4.77%).

Workup

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

Sources & evidence

ORD record
ord-041afe7205d8409fa2edffd0ce959e3b
Source dataset
uspto-grants-1993_10
Patent number
US05252575

Reaction notes

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