Reaktion #165680

Reaktionsgleichung

allyl bromide

solution

N-(5-tert-butylthiazol-2-yl)-5-chloro-2-methoxybenzamide

N,N-dimethylformamide

potassium tert-butoxide

→

title compound

N-[(2Z)-3-allyl-5-tert-butyl-1,3-thiazol-2(3H)-ylidene]-5-chloro-2-methoxybenzamide

Lösungsmittel

tetrahydrofuran

Reaktionsbedingungen

Aufarbeitung

1. 1
   workup.STIRRINGstirred overnight
2. 2
   TemperaturThe mixture was cooled to ambient temperature
3. 3
   Einengenconcentrated
4. 4
   workup.ADDITIONdiluted with CH2Cl2
5. 5
   Waschenwashed with water and brine
6. 6
   TrocknenThe organic layer was dried over magnesium sulfate
7. 7
   Filtrationfiltered
8. 8
   Einengenconcentrated under reduced pressure
9. 9
   SonstigePurification by chromatography (20-50% ethyl ccetate/hexane gradient)

Vorschrift

To a solution of Example 244A (410 mg, 1.3 mmol) in 5 mL of tetrahydrofuran:N,N-dimethylformamide (4/1) at 0° C. was added potassium tert-butoxide (230 mg, 1.9 mmol). The reaction mixture was stirred for 1 hour then allyl bromide (0.16 mL, 1.9 mmol) was added. The mixture was warmed to 65° C. and stirred overnight. The mixture was cooled to ambient temperature, concentrated, diluted with CH2Cl2 and washed with water and brine. The organic layer was dried over magnesium sulfate, filtered, and concentrated under reduced pressure. Purification by chromatography (20-50% ethyl ccetate/hexane gradient) afforded the title compound. 1H NMR (CDCl3, 300 MHz) δ ppm 1.34 (s, 9H), 3.90 (s, 3H), 4.78-4.85 (m, 3H), 5.22-5.36 (m, 2H), 5.90-6.09 (m, J=17.0, 10.17 Hz, 1H), 6.62 (s, 1H), 6.90 (d, J=9.2 Hz, 1H), 7.32 (dd, J=8.8, 3.1 Hz, 1H), 8.00 (d, J=2.7 Hz, 1H); MS (DCI/NH3) m/z 365 (M+H)+.

Quelle