Reaktion #2308285

Reaktionsgleichung

paraformaldehyde

compound 5D

tert-Butyl 2-((3-bromo-6-phenylpyridazin-4-yl)methyl)-3-oxobutanoate

lithium bis(trimethylsilyl)amide

→

tert-butyl 2-((3-bromo-6-phenylpyridazin-4-yl)methyl)acrylate

Ausbeute 97.0%

Lösungsmittel

THF

Reaktionsbedingungen

Aufarbeitung

1. 1
   SonstigeThe cooling bath was removed
2. 2
   SonstigeThe reaction mixture was then quenched with saturated NaCl
3. 3
   Extraktionextracted twice with dichloromethane
4. 4
   TrocknenThe combined organic extracts were dried over MgSO4
5. 5
   Filtrationfiltered
6. 6
   Sonstigeevaporated under reduced pressure
7. 7
   SonstigePurification by silica gel chromatography (7:93 Ether/CH2Cl2)

Vorschrift

To a stirred solution of compound 5D, (0.160 g, 0.39 mmol) in 3 mL of THF at room temperature under argon was added 0.43 mL (in THF, 0.43 mmol) of 1M lithium bis(trimethylsilyl)amide over 2 min and, after 20 min, powdered, dry paraformaldehyde (0.059 mg, 1.97 mmol). The cooling bath was removed and the reaction mixture was stirred at room temperature for 3 h. The reaction mixture was then quenched with saturated NaCl and extracted twice with dichloromethane. The combined organic extracts were dried over MgSO4, filtered and evaporated under reduced pressure. Purification by silica gel chromatography (7:93 Ether/CH2Cl2) provided the title compound, tert-butyl 2-((3-bromo-6-phenylpyridazin-4-yl)methyl)acrylate (0.142 g, 97%) as a light yellow oil. MS [M+H]+: found 375.

Quelle