Reaktion #443617

Reaktionsgleichung

chloromethyl methylsulfide

chloromethyl methylsulfide

compound

2-Chloro-N-ethyl-6-(trimethylsilyl)benzamide

sodium bis(trimethylsilyl)amide

→

colorless oil

Ausbeute 45.0%

2-Chloro-N-ethyl-N-[(methylthio)methyl]-6-(trimethylsilyl)benzamide

Ausbeute 45.0%

Lösungsmittel

THF

Reaktionsbedingungen

Aufarbeitung

1. 1
   workup.STIRRINGStirring at RT
2. 2
   Temperaturthe mixture was then heated
3. 3
   Temperaturto reflux for 28 hours
4. 4
   Sonstigewas then partitioned between ether and water
5. 5
   WaschenThe organic layer was washed with brine
6. 6
   Trocknendried (MgSO4)
7. 7
   Filtrationwas filtered through silica gel
8. 8
   SonstigeThe filtrate was evaporated in vacuo
9. 9
   Sonstigethe residue was chromatographed (HPLC, 8% ethyl acetate/hexane)

Vorschrift

To a solution of 2.0 g (7.8 mmol) of the compound of Example 45 in 30 mL dry THF was added 7.9 mL (7.9 mmol) sodium bis(trimethylsilyl)amide (1.0M in THF). To the resulting mixture was added 1.0 g (10.4 mmol) chloromethyl methylsulfide. The mixture was stirred for min and another 0.65 g (6.7 mmol) of chloromethyl methylsulfide was added. Stirring at RT was continued for 1 h and the mixture was then heated to reflux for 28 hours. The mixture was allowed to cool to RT and was then partitioned between ether and water. The organic layer was washed with brine, dried (MgSO4), and was filtered through silica gel. The filtrate was evaporated in vacuo and the residue was chromatographed (HPLC, 8% ethyl acetate/hexane) to yield 1.1 g (45%) of a colorless oil. nD25 =1.5526.

Quelle