Benzene, 1-chloro-4-ethynyl- → HCID 71255724, Verbindung

HRID 2202148Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 2202148
[Cl:1][C:2]1[CH:7]=[CH:6][C:5]([C:8]#[CH:9])=[CH:4][CH:3]=1.C([Li])CCC.CON(C)[C:18]([CH:20]1[CH2:25][CH2:24][N:23]([C:26]([O:28][C:29]([CH3:32])([CH3:31])[CH3:30])=[O:27])[CH2:22][CH2:21]1)=[O:19]>C1COCC1.O>[Cl:1][C:2]1[CH:7]=[CH:6][C:5]([C:8]#[C:9][C:18]([CH:20]2[CH2:25][CH2:24][N:23]([C:26]([O:28][C:29]([CH3:32])([CH3:31])[CH3:30])=[O:27])[CH2:22][CH2:21]2)=[O:19])=[CH:4][CH:3]=1

Komponenten

6

Edukt 3

HCID 70118Benzene, 1-chloro-4-ethynyl-HCID 11065582tert-Butyl 4-(methoxy(methyl)carbamoyl)piperidine-1-carboxylate2×HCID 178418339Butyllithium

Produkt 1

HCID 71255724HCID 71255724, Verbindung

Reagenzien, Katalysatoren, Lösungsmittel 2

HCID 962WaterLösungsmittelHCID 8028TetrahydrofuranLösungsmittel

Reaktionsbedingungen

Temperatur
-78 °C

Versuchsvorschrift

To a solution of 1-chloro-4-ethynylbenzene (2.76 g, 20.20 mmol) in THF (50 mL) at −78° C. was added 2.5 M butyllitium (8.81 ml, 22.03 mmol in hexane) and stirred for 1 h at −78° C. tert-Butyl 4-[methoxy(methyl)carbamoyl]piperidine-1-carboxylate (Compound 1.2, 5 g, 18.36 mmol) was added. The mixture was stirred at −78° C. for 30 min, then warmed up to 0° C., stirred for another hour at the same temperature, and diluted with water. The organic layer was separated and the aqueous was extracted with ethyl acetate. The combined organic layers were dried over Na2SO4, and the drying agent was filtered off. The filtrate was concentrated. The residue was purified by silica gel column chromatography using gradient elution (5 to 30%, EtOAc/hexane). LC-MS m/z 292.06 [M−56+H]+.

Aufarbeitung

  1. additionwas added
  2. temperaturewarmed up to 0° C.
  3. stirringstirred for another hour at the same temperature
  4. customThe organic layer was separated
  5. extractionthe aqueous was extracted with ethyl acetate
  6. dry with materialThe combined organic layers were dried over Na2SO4
  7. filtrationthe drying agent was filtered off
  8. concentrationThe filtrate was concentrated
  9. customThe residue was purified by silica gel column chromatography
  10. washelution (5 to 30%, EtOAc/hexane)

Quellen und Nachweise

ORD-Eintrag
ord-48e75d6d8e704b53aeabf7cef64777ea
Quelldatensatz
uspto-grants-2016_06
Patentnummer
US09365539B2

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