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

HRID 584390
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인쇄 미리보기

반응식

HRID 584390 반응식
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]
참가 물질실험 절차후처리출처 및 근거반응 노트

참가 물질

7

반응물 4

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

생성물 1

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

시약·촉매·용매 2

HCID 8028
Tetrahydrofuran
용매
HCID 22262317Ethyl acetate hexane toluene용매

실험 절차

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.

후처리

  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

출처 및 근거

ORD 기록
ord-458065fe40b9472b9ca7dd1004023bbc
출처 데이터셋
uspto-grants-2005_08
DOI
10.6084/m9.figshare.5104873.v1
특허 번호
US06924300B2

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