N-Hydroxyphthalimide → N-[4-(tert-butyldimethylsilyloxy)benzyloxy]phthalimide

HRID 2299748Notes

Reaction equation

HRID 2299748 reaction equation
N(C(OCC)=O)=NC(OCC)=O.[Si:13]([O:20][C:21]1[CH:28]=[CH:27][C:24]([CH2:25][OH:26])=[CH:23][CH:22]=1)([C:16]([CH3:19])([CH3:18])[CH3:17])([CH3:15])[CH3:14].O[N:30]1[C:34](=[O:35])[C:33]2=[CH:36][CH:37]=[CH:38][CH:39]=[C:32]2[C:31]1=[O:40].C1(P(C2C=CC=CC=2)C2C=CC=CC=2)C=CC=CC=1>O1CCCC1.C(OCC)(=O)C.CCCCCC.C1(C)C=CC=CC=1>[Si:13]([O:20][C:21]1[CH:28]=[CH:27][C:24]([CH2:25][O:26][N:30]2[C:31](=[O:40])[C:32]3=[CH:39][CH:38]=[CH:37][CH:36]=[C:33]3[C:34]2=[O:35])=[CH:23][CH:22]=1)([C:16]([CH3:19])([CH3:18])[CH3:17])([CH3:15])[CH3:14]

Participants

7

Reactant 4

HCID 10665N-HydroxyphthalimideHCID 11776TriphenylphosphineHCID 220568ethyl N-ethoxycarbonyliminocarbamateHCID 10014460(4-((Tert-butyldimethylsilyl)oxy)phenyl)methanol

Product 1

HCID 11825150N-[4-(tert-butyldimethylsilyloxy)benzyloxy]phthalimideYield 44.1%

Reagents, catalysts & solvents 2

HCID 8028TetrahydrofuranSolventHCID 22262317Ethyl acetate hexane tolueneSolvent

Procedure

Diethyl azodicarboxylate (40% toluene solution, 54.0 g) was added dropwise to a solution of 4-(tert-butyldimethylsilyloxy)benzylalcohol (27.5 g), N-hydroxyphthalimide (16.8 g) and triphenylphosphine (31.1 g) in tetrahydrofuran (450 ml) at room temperature and stirred for 18 hours. After the reaction mixture was concentrated, diisopropyl ether (200 ml) was added and the residual crystals were removed by filtration. The filtrate was concentrated, and the residue was subjected to silica gel chromatography to obtain N-[4-(tert-butyldimethylsilyloxy)benzyloxy]phthalimide (17.4 g, yield 43%) as crystals from an ethyl acetate-hexane-toluene (1:10:10, v/v)-eluted fraction. The crystals were recrystallized from ethyl acetate-hexane to obtain colorless crystals. m.p. 76-77° C.

Workup

  1. concentrationAfter the reaction mixture was concentrated
  2. additiondiisopropyl ether (200 ml) was added
  3. customthe residual crystals were removed by filtration
  4. concentrationThe filtrate was concentrated

Sources & evidence

ORD record
ord-002b1451c37441d8933b9473c5294726
Source dataset
uspto-grants-2002_12
Patent number
US06495581B1

Reaction notes

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