StartseiteMCPWorkbenchSkills
StartseiteWorkbenchBenachrichtigungenMein Bereich
llms.txt · MCP-AnleitungDatenschutz · Nutzungsbedingungen · Supportv1.8.0
  1. Startseite
  2. /Reaktion

2-Chloromethyl 2-(trimethylsilyl)ethyl ether → HCID 68354670, Verbindung

HRID 513105
Notizen
Druckvorschau

Reaktionsgleichung

Reaktionsgleichung von HRID 513105
[N:1]1([C:11]([O:13][C:14]([CH3:17])([CH3:16])[CH3:15])=[O:12])[CH2:6][CH2:5][O:4][CH:3]([C:7]([O:9][CH3:10])=[O:8])[CH2:2]1.[Li+].C[Si]([N-][Si](C)(C)C)(C)C.Cl[CH2:29][O:30][CH2:31][CH2:32][Si:33]([CH3:36])([CH3:35])[CH3:34]>C1COCC1>[CH3:34][Si:33]([CH3:36])([CH3:35])[CH2:32][CH2:31][O:30][CH2:29][C:3]1([C:7]([O:9][CH3:10])=[O:8])[O:4][CH2:5][CH2:6][N:1]([C:11]([O:13][C:14]([CH3:17])([CH3:16])[CH3:15])=[O:12])[CH2:2]1
KomponentenReaktionsbedingungenVersuchsvorschriftAufarbeitungQuellen und NachweiseNotizen zur Reaktion

Komponenten

5

Edukt 3

HCID 27242712-Chloromethyl 2-(trimethylsilyl)ethyl etherHCID 2733832Lithium hexamethyldisilazaneHCID 588174744-tert-Butyl 2-methyl morpholine-2,4-dicarboxylate

Produkt 1

HCID 68354670HCID 68354670, VerbindungAusbeute 80 %

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 8028TetrahydrofuranLösungsmittel

Reaktionsbedingungen

Temperatur
-78 °C

Versuchsvorschrift

E1 (5.0 g 20.39 mmol) was dissolved in THF (45 mL) and cooled to −78° C. LHMDS (1 M in hexane/ethylbenzene) (40.8 mL, 40.8 mmol) was added in 30 minutes and the solution was stirred for 35 min at −78° C. (2-(Chloromethoxy)ethyl)trimethylsilane (10.02 mL, 56.5 mmol) was added and the reaction mixture was allowed to warm to room temperature overnight. The reaction mixture was quenched with saturated NH4Cl and extracted twice with EtOAc. The organic layer was washed with brine, dried over MgSO4, filtered and concentrated in vacuo. The residue was purified by flash column chromatography (heptane:EtOAc=100:0 to 70:30) yielding the title compound (6.09 g, 80%). 1H NMR (400 MHz, CDCl3, 300K): δ 0.00 (3H, s), 0.92 (2H, t, J=7.5 Hz), 1.47 (9H, s), 3.02 (2H, d, J=13.3 Hz), 3.55 (4H, m), 3.78 (3H, s), 3.83 (3H, m), 4.34 (1H, d, J=13.3 Hz). MS (ES) C17H33NO6Si requires: 375. found: 398.2 [M+Na]+.

Aufarbeitung

  1. additionwas added
  2. temperatureto warm to room temperature overnight
  3. customThe reaction mixture was quenched with saturated NH4Cl
  4. extractionextracted twice with EtOAc
  5. washThe organic layer was washed with brine
  6. dry with materialdried over MgSO4
  7. filtrationfiltered
  8. concentrationconcentrated in vacuo
  9. customThe residue was purified by flash column chromatography (heptane:EtOAc=100:0 to 70:30)

Quellen und Nachweise

ORD-Eintrag
ord-78b9975fc24741b5b6ee981dc9c747b5
Quelldatensatz
uspto-grants-2015_08
DOI
10.6084/m9.figshare.5104873.v1
Patentnummer
US09102676B2

Notizen zur Reaktion

Wird geladen…

Auf dieser SeiteKomponentenReaktionsbedingungenVersuchsvorschriftAufarbeitungQuellen und NachweiseNotizen zur Reaktion