Phthalimide → HCID 15225542, compound

HRID 260635Notes

Reaction equation

HRID 260635 reaction equation
[CH2:1]([Si:8]([CH3:13])([CH3:12])[CH2:9][CH2:10]O)[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.[C:14]1(=[O:24])[NH:18][C:17](=[O:19])[C:16]2=[CH:20][CH:21]=[CH:22][CH:23]=[C:15]12.CCOC(/N=N/C(OCC)=O)=O.C1(P(C2C=CC=CC=2)C2C=CC=CC=2)C=CC=CC=1>O1CCCC1>[CH2:1]([Si:8]([CH3:13])([CH3:12])[CH2:9][CH2:10][N:18]1[C:17](=[O:19])[C:16]2=[CH:20][CH:21]=[CH:22][CH:23]=[C:15]2[C:14]1=[O:24])[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1

Participants

6

Reactant 4

HCID 6809PhthalimideHCID 11776TriphenylphosphineHCID 5462977Diethyl azodicarboxylateHCID 15338763HCID 15338763, compound

Product 1

HCID 15225542HCID 15225542, compoundYield 67.1%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

A mixture of β-(benzyldimethylsilyl)ethanol (0.84 g, 4.33 mmol), phthalimide (0.66 g, 4.5 mmol), diethylazodicarboxylate (0.783 g, 4.5 mmol) and triphenylphosphine (1.18 g, 4.5 mmol) in anhydrous tetrahydrofuran (80 ml) is stirred, under nitrogen, at room temperature for 18 hours. The solvent is removed in vacuo. The residue is taken off in toluene and the insoluble material is filtered off. The filtrate is evaporated to dryness. The residue is taken off in diethyl ether and the insoluble material is filtered off. The solvent is removed in vacuo. Chromatography (silica gel, hexane/diethyl ether-80/20) affords the title compound (0.94 g, 67% yield).

Workup

  1. customThe solvent is removed in vacuo
  2. filtrationthe insoluble material is filtered off
  3. customThe filtrate is evaporated to dryness
  4. filtrationthe insoluble material is filtered off
  5. customThe solvent is removed in vacuo

Sources & evidence

ORD record
ord-645801a20e794a60aa0a3781e9fe8369
Source dataset
uspto-grants-1996_06
Patent number
US05529988

Reaction notes

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