Reaktion #358487

Reaktionsgleichung

tert-Butylsulphinamide

product

3-chloro-4-{(E)-2-[5-(4-fluorophenyl)-1-methyl-1H-pyrazol-3-yl]vinyl}bicyclo[4.2.1]non-3-en-9-one

ethyl acetate

→

N((9Z)-3-chloro-4-{(E)-2-[5-(4-fluorophenyl)-1-methyl-1H-pyrazol-3-yl]vinyl}bicyclo[4.2.1]non-3-en-9-ylidene)-2-methylpropane-2-sulfinamide

Ausbeute 99.5%

Lösungsmittel

brine

THF

Reaktionsbedingungen

Aufarbeitung

1. 1
   Temperaturthe resulting solution was heated
2. 2
   Temperaturto reflux for 18 hrs
3. 3
   Filtrationthe mixture filtered through celite
4. 4
   SonstigeThe filtrate was partitioned
5. 5
   Extraktionthe aqueous layer was further extracted with ethyl acetate (2×50 ml)
6. 6
   ExtraktionThe combined organic extract
7. 7
   Waschenwas washed with brine
8. 8
   Trocknendried over MgSO4
9. 9
   Einengenconcentrated in vacuo

Vorschrift

tert-Butylsulphinamide (3.0, 24 mmol) followed by titanium (IV) ethoxide (4.6 ml, 36 mmol) was added to a stirring solution of the product of Step 3 (4.56 g, 11 mmol) in dry THF (10 ml) and the resulting solution was heated to reflux for 18 hrs. The reaction was poured into a stirring solution of brine (200 ml) and then ethyl acetate (100 ml) was added and the mixture filtered through celite. The filtrate was partitioned and the aqueous layer was further extracted with ethyl acetate (2×50 ml). The combined organic extract was washed with brine, dried over MgSO4 and concentrated in vacuo, to afford N((9Z)-3-chloro-4-{(E)-2-[5-(4-fluorophenyl)-1-methyl-1H-pyrazol-3-yl]vinyl}bicyclo[4.2.1]non-3-en-9-ylidene)-2-methylpropane-2-sulfinamide (5.19 g, 99%). m/z (ES+) 474 (MH)+. Compound taken directly onto next Step.

Quelle