Triethylamine → 4-(3-((Tert-butyldimethylsilyloxy)methyl)-4-nitrophenyl)morpholine

HRID 1487195Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 1487195
[O:1]1[CH2:6][CH2:5][N:4]([C:7]2[CH:8]=[CH:9][C:10]([N+:15]([O-:17])=[O:16])=[C:11]([CH2:13][OH:14])[CH:12]=2)[CH2:3][CH2:2]1.C(N(CC)CC)C.[C:25]([Si:29](Cl)([CH3:31])[CH3:30])([CH3:28])([CH3:27])[CH3:26]>CN(C)C1C=CN=CC=1.ClCCl.C(OCC)(=O)C>[Si:29]([O:14][CH2:13][C:11]1[CH:12]=[C:7]([N:4]2[CH2:5][CH2:6][O:1][CH2:2][CH2:3]2)[CH:8]=[CH:9][C:10]=1[N+:15]([O-:17])=[O:16])([C:25]([CH3:28])([CH3:27])[CH3:26])([CH3:31])[CH3:30]

Komponenten

7

Edukt 3

HCID 8471TriethylamineHCID 28928tert-Butyldimethylsilyl chlorideHCID 9878047(5-Morpholin-4-YL-2-nitro-phenyl)-methanol

Produkt 1

HCID 866996854-(3-((Tert-butyldimethylsilyloxy)methyl)-4-nitrophenyl)morpholineAusbeute 90,9 %

Reagenzien, Katalysatoren, Lösungsmittel 3

HCID 142844-(Dimethylamino)pyridineKatalysatorHCID 6344DichloromethaneLösungsmittelHCID 8857Ethyl AcetateLösungsmittel

Versuchsvorschrift

To a solution of (5-morpholino-2-nitrophenyl)methanol (3.0 g, 12.6 mmol), triethylamine (2.54 g, 25.2 mmol) and 4-dimethylaminopyridine (0.2 g) in dichloromethane (100 mL) was added tert-butylchlorodimethylsilane (2.83 g, 18.9 mmol). After the addition was over, the mixture was stirred at room temperature for 2 hours. The reaction mixture was diluted with ethyl acetate, and the organic phase was washed by saturated sodium bicarbonate, dried over anhydrous sodium sulfate, evaporated and purified by silica gel chromatography to afford the product 4-(3-((tert-butyldimethylsilyloxy)methyl)-4-nitrophenyl)morpholine (4.0 g, yield 90.9%).

Aufarbeitung

  1. additionAfter the addition
  2. washthe organic phase was washed by saturated sodium bicarbonate
  3. dry with materialdried over anhydrous sodium sulfate
  4. customevaporated
  5. custompurified by silica gel chromatography

Quellen und Nachweise

ORD-Eintrag
ord-ccaa05a926ba49a38405e9ef64798303
Quelldatensatz
uspto-grants-2016_08
Patentnummer
US09428508B2

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