Reaktion #1559065

Reaktionsgleichung

2-(2-bromoethoxy)tetrahydro-2H-pyran

hydrazine hydrate

2-(3-methoxyphenyl)-1-phenylethanone

potassium tert-butoxide

Acetic acid

CS2

→

title compound

Ausbeute 74.2%

4-(3-Methoxyphenyl)-3-phenyl-5-(2-(tetrahydro-2H-pyran-2-yloxy)ethylthio)-1H-pyrazole

Ausbeute 74.2%

Lösungsmittel

ethanol

THF

Reaktionsbedingungen

Aufarbeitung

1. 1
   workup.ADDITIONwas added
2. 2
   workup.STIRRINGThe reaction was stirred at 85° C. overnight
3. 3
   Einengenconcentrated under reduced pressure
4. 4
   ExtraktionThe residue was extracted with EtOAc/H2O (twice)
5. 5
   Waschenwashed with brine
6. 6
   Trocknendried over MgSO4
7. 7
   Einengenconcentrated
8. 8
   SonstigeThe residue was purified by silica gel column chromatography

Vorschrift

To a stirred solution of 2-(3-methoxyphenyl)-1-phenylethanone (1.25 g, 5.52 mmol) in THF (11.05 mL) was added potassium tert-butoxide (11.49 mL, 11.49 mmol). After 30 min, CS2 (0.363 mL, 6.02 mmol) was added and the mixture was stirred for 10 min before 2-(2-bromoethoxy)tetrahydro-2H-pyran (2.086 mL, 13.81 mmol) was added and the reaction was stirred overnight. The mixture was diluted with ethanol (11.05 mL). Acetic acid (1.898 mL, 33.1 mmol) was added followed by hydrazine hydrate (2.71 mL, 55.2 mmol). The reaction was stirred at 85° C. overnight and concentrated under reduced pressure. The residue was extracted with EtOAc/H2O (twice). The organic phases were combined and washed with brine, dried over MgSO4 and concentrated. The residue was purified by silica gel column chromatography to give the title compound as a white solid (1.681 g). 1H NMR (400 MHz, CDCl3) δ ppm 1.52-1.64 (m, 3H), 1.65-1.93 (m, 3H), 3.06 (t, J=5.94 Hz, 2H), 3.49-3.57 (m, 1H), 3.65-3.71 (m, 1H), 3.72 (s, 3H), 3.88-3.95 (m, 1H), 3.97-4.05 (m, 1H), 4.66-4.69 (m, 1H), 6.79-6.90 (m, 3H), 7.19-7.26 (m, 1H), 7.26-7.33 (m, 3H), 7.37-7.45 (m, 2H), 10.91 (bs, 1H).

Quelle