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2-Methoxyethanol → Tert-butyl 2-(3-(2-methoxyethoxy)quinolin-6-yl)acetate

HRID 40351
Notizen
Druckvorschau

Reaktionsgleichung

Reaktionsgleichung von HRID 40351
[OH:1][C:2]1[CH:3]=[N:4][C:5]2[C:10]([CH:11]=1)=[CH:9][C:8]([CH2:12][C:13]([O:15][C:16]([CH3:19])([CH3:18])[CH3:17])=[O:14])=[CH:7][CH:6]=2.C1(P(C2C=CC=CC=2)C2C=CC=CC=2)C=CC=CC=1.[CH3:39][O:40][CH2:41][CH2:42]O.N(C(OC(C)(C)C)=O)=NC(OC(C)(C)C)=O>CCOC(C)=O.C1C=CC=CC=1>[CH3:39][O:40][CH2:41][CH2:42][O:1][C:2]1[CH:3]=[N:4][C:5]2[C:10]([CH:11]=1)=[CH:9][C:8]([CH2:12][C:13]([O:15][C:16]([CH3:19])([CH3:18])[CH3:17])=[O:14])=[CH:7][CH:6]=2
KomponentenReaktionsbedingungenVersuchsvorschriftAufarbeitungQuellen und NachweiseNotizen zur Reaktion

Komponenten

7

Edukt 4

HCID 80192-MethoxyethanolHCID 11776TriphenylphosphineHCID 97268Di-tert-butyl azodicarboxylateHCID 57691372Tert-butyl 2-(3-hydroxyquinolin-6-yl)acetate

Produkt 1

HCID 57690925Tert-butyl 2-(3-(2-methoxyethoxy)quinolin-6-yl)acetateAusbeute 82 %

Reagenzien, Katalysatoren, Lösungsmittel 2

HCID 241
Benzene
Lösungsmittel
HCID 8857Ethyl AcetateLösungsmittel2×

Reaktionsbedingungen

Temperatur
0 °C

Versuchsvorschrift

A flask was charged with tert-butyl 2-(3-hydroxyquinolin-6-yl)acetate (581.04 mg, 2.241 mmol) and triphenylphosphine (1.175 g, 4.482 mmol) then sealed with a septum and an placed under N2. Benzene (10 mL) was added, followed by 2-methoxyethanol (0.8838 ml, 11.20 mmol). The heterogeneous solution was cooled to 0° C., and di-tert-butyl azodicarboxylate (1.032 g, 4.482 mmol) was added as a solid in a single portion. The solution was allowed to warm to rt and maintained 20 h. The solution was then partitioned between saturated aqueous. NH4Cl, and the layers separated. The aqueous layer was extracted with EtOAc (2×50 mL), and the combined organic layers were washed with brine, dried (MgSO4), and concentrated in vacuo. The resulting residue was purified by MPLC (Teledine Isco combiFlash Companion), 80 g SiO2, solvent system: 90:10 hexanes:EtOAc gradient to 50:50 hexanes:EtOAc to give tert-butyl 2-(3-(2-methoxyethoxy)quinolin-6-yl)acetate (585. 2 mg, 82% yield). LRMS (ESI) m/z calcd for C18H24NO4 (M+H) 318.2. found 318.3.

Aufarbeitung

  1. customthen sealed with a septum
  2. temperatureto warm to rt
  3. temperaturemaintained 20 h
  4. customThe solution was then partitioned between saturated aqueous
  5. customNH4Cl, and the layers separated
  6. extractionThe aqueous layer was extracted with EtOAc (2×50 mL)
  7. washthe combined organic layers were washed with brine
  8. dry with materialdried (MgSO4)
  9. concentrationconcentrated in vacuo
  10. customThe resulting residue was purified by MPLC (Teledine Isco combiFlash Companion), 80 g SiO2, solvent system

Quellen und Nachweise

ORD-Eintrag
ord-8dfdfb4c74224e3191f4dafaaac5c262
Quelldatensatz
uspto-grants-2013_09
DOI
10.6084/m9.figshare.5104873.v1
Patentnummer
US08524900B2

Notizen zur Reaktion

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