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Water → 2-{[tert-butyl(dimethyl)silyl]oxy}-N-(5-methylpyridin-2-yl)hexanamide

HRID 1098073
Notizen
Druckvorschau

Reaktionsgleichung

Reaktionsgleichung von HRID 1098073
[Li]CCCC.[NH2:6][C:7]1[CH:12]=[CH:11][C:10]([CH3:13])=[CH:9][N:8]=1.[Si:14]([O:21][CH:22]([CH2:28][CH2:29][CH2:30][CH3:31])[C:23](OCC)=[O:24])([C:17]([CH3:20])([CH3:19])[CH3:18])([CH3:16])[CH3:15].O>C1COCC1.CCOC(C)=O>[Si:14]([O:21][CH:22]([CH2:28][CH2:29][CH2:30][CH3:31])[C:23]([NH:6][C:7]1[CH:12]=[CH:11][C:10]([CH3:13])=[CH:9][N:8]=1)=[O:24])([C:17]([CH3:20])([CH3:19])[CH3:18])([CH3:15])[CH3:16]
KomponentenVersuchsvorschriftAufarbeitungQuellen und NachweiseNotizen zur Reaktion

Komponenten

7

Edukt 4

HCID 962WaterHCID 153482-Amino-5-methylpyridineHCID 57438620Ethyl 2-{[tert-butyl(dimethyl)silyl]oxy}hexanoateHCID 178418339Butyllithium

Produkt 1

HCID 575045712-{[tert-butyl(dimethyl)silyl]oxy}-N-(5-methylpyridin-2-yl)hexanamideAusbeute 22,1 %

Reagenzien, Katalysatoren, Lösungsmittel 2

HCID 8028
Tetrahydrofuran
Lösungsmittel
2×
HCID 8857Ethyl AcetateLösungsmittel

Versuchsvorschrift

n-BuLi (2.25 mL, 1.6 M in hexanes, 3.60 mmol) was added slowly to a stirred solution of 2-amino-5-picoline (390 mg, 3.60 mmol) in anhydrous THF (6 mL). The reaction mixture was kept at ambient temperature for 10 minutes before it was added to a solution of ethyl 2-{[tert-butyl(dimethyl)silyl]oxy}hexanoate (Step 1) (820 mg, 3.00 mmol) in anhydrous THF (4 mL). The reaction mixture was stirred at ambient temperature for 1 h. Water and EtOAc were added and the two phases were separated. The organic phase was washed with water, dried over MgSO4 and concentrated in vacuo. The residue was purified with column chromatography (silica gel, eluting with a gradient consisting of 0-100% EtOAc in heptane) to give the title compound as a colourless oil (223 mg), 1H NMR (300 MHz, CDCl3) δ 8.87 (br s, 1H), 8.13 (m, 2H), 7.51 (dd, 1H), 4.25 (t, 1H), 2.29 (s, 3H), 1.79 (m, 2H), 1.35 (m, 4H), 0.98 (s, 8H), 0.89 (t, 3H), 0.14 (d, 6H).

Aufarbeitung

  1. customthe two phases were separated
  2. washThe organic phase was washed with water
  3. dry with materialdried over MgSO4
  4. concentrationconcentrated in vacuo
  5. customThe residue was purified with column chromatography (silica gel
  6. washeluting with

Quellen und Nachweise

ORD-Eintrag
ord-cdbf8aded7464d8f92257e348539deaf
Quelldatensatz
uspto-grants-2012_03
DOI
10.6084/m9.figshare.5104873.v1
Patentnummer
US08143263B2

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