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

HRID 584390Notes

Reaction equation

HRID 584390 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-458065fe40b9472b9ca7dd1004023bbc
Source dataset
uspto-grants-2005_08
Patent number
US06924300B2

Reaction notes

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