N-Hydroxyphthalimide → HCID 13989886, compound

HRID 1089243Notes

Reaction equation

HRID 1089243 reaction equation
N(C(OCC)=O)=NC(OCC)=O.[CH2:13]([O:20][CH2:21][CH2:22][CH2:23][OH:24])[C:14]1[CH:19]=[CH:18][CH:17]=[CH:16][CH:15]=1.O[N:26]1[C:30](=[O:31])[C:29]2=[CH:32][CH:33]=[CH:34][CH:35]=[C:28]2[C:27]1=[O:36].C1(P(C2C=CC=CC=2)C2C=CC=CC=2)C=CC=CC=1>O1CCCC1>[CH2:13]([O:20][CH2:21][CH2:22][CH2:23][O:24][N:26]1[C:27](=[O:36])[C:28]2=[CH:35][CH:34]=[CH:33][CH:32]=[C:29]2[C:30]1=[O:31])[C:14]1[CH:19]=[CH:18][CH:17]=[CH:16][CH:15]=1

Participants

6

Reactant 4

HCID 10665N-HydroxyphthalimideHCID 11776TriphenylphosphineHCID 220568ethyl N-ethoxycarbonyliminocarbamateHCID 3479713-Benzyloxy-1-propanol

Product 1

HCID 13989886HCID 13989886, compoundYield 99.1%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

Diethyl azodicarboxylate (15.6 ml 99.4 mmol) added to a solution of 3-benzyloxy-1-propanol (15 g, 90.4 mmol), N-hydroxyphthalimide (14.7 g, 90.1 mmol) and triphenylphosphine (23.7 g, 90.4 mmol) in tetrahydrofuran (450 ml). After 16 hours at 20° C. the solvent was removed under reduced pressure and the residue chromatographed on silica gel (eluted with hexane:acetone, 3:1) to yield the title compound as a yellow oil (27.8 g, 99%).

Workup

  1. customAfter 16 hours at 20° C. the solvent was removed under reduced pressure
  2. customthe residue chromatographed on silica gel (eluted with hexane:acetone, 3:1)

Sources & evidence

ORD record
ord-73289466ad2c462a9b3596a13513e6ff
Source dataset
uspto-grants-1990_10
Patent number
US04965270

Reaction notes

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