Potassium Carbonate → HCID 86725582, Verbindung

HRID 514458

Reaktionsgleichung

Reaktionsgleichung von HRID 514458
[Cl:1][C:2]1[CH:3]=[CH:4][C:5]([CH2:9][OH:10])=[C:6]([OH:8])[CH:7]=1.I[CH2:12][CH2:13][CH3:14].C([O-])([O-])=O.[K+].[K+]>CN(C=O)C>[Cl:1][C:2]1[CH:3]=[CH:4][C:5]([CH2:9][OH:10])=[C:6]([O:8][CH2:12][CH2:13][CH3:14])[CH:7]=1

Komponenten

5

Edukt 3

HCID 11430Potassium CarbonateHCID 336431-IodopropaneHCID 3271485-Chloro-2-(hydroxymethyl)phenol

Produkt 1

HCID 86725582HCID 86725582, VerbindungAusbeute 58 %

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 6228DimethylformamideLösungsmittel

Reaktionsbedingungen

Temperatur
100 °C

Versuchsvorschrift

Charge 5-chloro-2-(hydroxymethyl)phenol (997 mg, 6.29 mmol, PREPARATION 7), iodopropane (1.17 g, 6.92 mmol), K2CO3 (1.74 g, 12.58 mmol) and DMF (6 mL) to a sealed tube. The reaction mixture was heated to 100° C. overnight. It was then poured into ice-water and extracted with ethyl acetate twice, washed the organic phase with water twice, brine and dried with Na2SO4, concentrated and purified by silica gel chromatograph to give the title compound (729 mg, 58%). 1H NMR (400 MHz, CDCl3): δ 1.05 (3H, t, J=7.2 Hz), 1.79-1.88 (2H, m), 3.96 (2H, t, J=6.4 Hz), 4.64 (2H, s), 6.85 (1H, d, J=1.2 Hz), 6.91 (1H, dd, J=1.6 Hz, 8.4 Hz), 7.20 (1H, d, J=8.0 Hz).

Aufarbeitung

  1. extractionextracted with ethyl acetate twice
  2. washwashed the organic phase with water twice
  3. dry with materialbrine and dried with Na2SO4
  4. concentrationconcentrated
  5. custompurified by silica gel chromatograph

Quellen und Nachweise

ORD-Eintrag
ord-0d4dfb69545f4815926283b358c2a4fc
Quelldatensatz
uspto-grants-2015_08
Patentnummer
US09107916B2

Verknüpfte Notizen

Wird geladen…