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Tetrabutylammonium Fluoride → 1-[4-(1-Ethyl-1-{4-[(2-methanesulfonylethylamino)methyl]-3-methylphenyl}propyl)-2-methylphenoxy]-3,3-dimethylbutan-2-ol

HRID 230813
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인쇄 미리보기

반응식

HRID 230813 반응식
[Si]([O:8][CH:9]([C:39]([CH3:42])([CH3:41])[CH3:40])[CH2:10][O:11][C:12]1[CH:17]=[CH:16][C:15]([C:18]([C:23]2[CH:36]=[CH:35][C:26]([CH2:27][NH:28][CH2:29][CH2:30][S:31]([CH3:34])(=[O:33])=[O:32])=[C:25]([CH3:37])[CH:24]=2)([CH2:21][CH3:22])[CH2:19][CH3:20])=[CH:14][C:13]=1[CH3:38])(C(C)(C)C)(C)C.CCCC[N+](CCCC)(CCCC)CCCC.[F-]>C1COCC1.O>[CH2:19]([C:18]([C:15]1[CH:16]=[CH:17][C:12]([O:11][CH2:10][CH:9]([OH:8])[C:39]([CH3:40])([CH3:42])[CH3:41])=[C:13]([CH3:38])[CH:14]=1)([C:23]1[CH:36]=[CH:35][C:26]([CH2:27][NH:28][CH2:29][CH2:30][S:31]([CH3:34])(=[O:33])=[O:32])=[C:25]([CH3:37])[CH:24]=1)[CH2:21][CH3:22])[CH3:20]
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참가 물질

5

반응물 2

HCID 2724141Tetrabutylammonium FluorideHCID 68464086[4-(1-{4-[2-(t-Butyldimethylsilanyloxy)-3,3-dimethylbutoxy]-3-methylphenyl}-1-ethylpropyl)-2-methylbenzyl]-(2-methanesulfonylethyl)amine

생성물 1

HCID 100976061-[4-(1-Ethyl-1-{4-[(2-methanesulfonylethylamino)methyl]-3-methylphenyl}propyl)-2-methylphenoxy]-3,3-dimethylbutan-2-ol수율 79.4%

시약·촉매·용매 2

HCID 962Water용매
HCID 8028
Tetrahydrofuran
용매

실험 절차

To a mixture of [4-(1-{4-[2-(t-butyldimethylsilanyloxy)-3,3-dimethylbutoxy]-3-methylphenyl}-1-ethylpropyl)-2-methylbenzyl]-(2-methanesulfonylethyl)amine (1.47 g, 2.43 mmol) in THF (30 mL) is added 1M TBAF (2.7 mL, 2.7 mmol), and refluxed for 2 h. After cooling to RT, the mixture is diluted with H2O (20 mL) and extracted with EtOAc (3×30 mL). The combined organic layers are MgSO4 dried, concentrated, and chromatographed (80% EtOAc/Hex) to give the title compound (0.97 g, 1.93 mmol, 79%).

후처리

  1. temperaturerefluxed for 2 h
  2. extractionextracted with EtOAc (3×30 mL)
  3. customdried
  4. concentrationconcentrated
  5. customchromatographed (80% EtOAc/Hex)

출처 및 근거

ORD 기록
ord-6e75a6d1238b40f4b912ebf995c6c0f3
출처 데이터셋
uspto-grants-2009_07
DOI
10.6084/m9.figshare.5104873.v1
특허 번호
US07566803B2

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