N-Hydroxyphthalimide → HCID 22633854, compound

HRID 2417289Notes

Reaction equation

HRID 2417289 reaction equation
[OH:1][N:2]1[C:6](=[O:7])[C:5]2=[CH:8][CH:9]=[CH:10][CH:11]=[C:4]2[C:3]1=[O:12].C1(P(C2C=CC=CC=2)C2C=CC=CC=2)C=CC=CC=1.[CH3:32][O:33][C:34]1[CH:67]=[CH:66][C:37]([C:38]([O:53][CH2:54][CH2:55][O:56][CH2:57][CH2:58][O:59][CH2:60][CH2:61][O:62][CH2:63][CH2:64]O)([C:47]2[CH:52]=[CH:51][CH:50]=[CH:49][CH:48]=2)[C:39]2[CH:44]=[CH:43][C:42]([O:45][CH3:46])=[CH:41][CH:40]=2)=[CH:36][CH:35]=1.CCOC(/N=N/C(OCC)=O)=O>C1COCC1>[CH3:46][O:45][C:42]1[CH:41]=[CH:40][C:39]([C:38]([O:53][CH2:54][CH2:55][O:56][CH2:57][CH2:58][O:59][CH2:60][CH2:61][O:62][CH2:63][CH2:64][O:1][N:2]2[C:3](=[O:12])[C:4]3=[CH:11][CH:10]=[CH:9][CH:8]=[C:5]3[C:6]2=[O:7])([C:47]2[CH:52]=[CH:51][CH:50]=[CH:49][CH:48]=2)[C:37]2[CH:36]=[CH:35][C:34]([O:33][CH3:32])=[CH:67][CH:66]=2)=[CH:44][CH:43]=1

Participants

6

Reactant 4

HCID 10665N-HydroxyphthalimideHCID 11776TriphenylphosphineHCID 5462977Diethyl azodicarboxylateHCID 22633851HCID 22633851, compound

Product 1

HCID 22633854HCID 22633854, compoundYield 81.8%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

N-hydroxyphthalimide (0.7 g, 4.3 mmol) and triphenyl-phosphine (1.1 g, 4.2 mmol) were added to a solution of 11-(4,4′-dimethoxytrityloxy)-3,6,9-trioxaundecanol (2.0 g, 4.0 mmol) in THF (60 mL). Diethylazodicarboxylate (DEAD, 0.7 mL, 3.6 mmol) was added dropwise and the stirring was continued overnight at ambient temperature. The reaction mixture was evaporated to an oil, applied onto a silica gel column, and eluted with a linear gradient from neat CH2Cl2 to a 97:3 (v/v) mixture of CH2Cl2 and MeOH. The purification was repeated to yield 2.1 g (80%) of the title compound.

Workup

  1. customThe reaction mixture was evaporated to an oil
  2. washeluted with a linear gradient from neat CH2Cl2 to a 97:3 (v/v) mixture of CH2Cl2 and MeOH
  3. customThe purification

Sources & evidence

ORD record
ord-81fbc13ccb6b4459a0c7a2d52bdbf1f0
Source dataset
uspto-grants-2004_11
Patent number
US06825331B2

Reaction notes

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