Reacción #58528

Ecuación de reacción

NaHCO3

product

2-Benzyl-5,6-dibromo-1,2,3,3a,7,7a-hexahydro-4-thia-2-aza-cyclopenta[α]pentalen-7-ol

chlorodiphenylsilane

→

subtitle compound

2-Benzyl-5,6-dibromo-1,2,3,3a,7,7a-hexahydro-4-thia-2-aza-cyclopenta[α]pentalene

Disolventes

EtOAc

dichloroethane

Condiciones de reacción

Tratamiento posterior

1. 1
   TemperaturaThe reaction mixture was cooled to 22° C.
2. 2
   Otroproducing a white emulsion
3. 3
   Otrothe organic layer was separated
4. 4
   Lavadowashed with brine (25 ml)
5. 5
   Secadodried (MgSO4)
6. 6
   workup.DISSOLUTIONThe crude product was dissolved in 7:3 hexanes

Procedimiento

The product from step f) (300 mg, 0.69 mmol) in dichloroethane (2.6 ml) was treated with InCl3 (153 mg, 0.69 mmol) and chlorodiphenylsilane (457 mg, 2.08 mmol). The contents were heated to 60° C. for 16 hours. The reaction mixture was cooled to 22° C., poured into sat. NaHCO3 and diluted with EtOAc (75 ml); producing a white emulsion. The emulsion was passed through celite and the organic layer was separated, washed with brine (25 ml) and dried (MgSO4). The crude product was dissolved in 7:3 hexanes:EtOAc and passed through a plug of silica gel to give the subtitle compound. MS calculated for C16H15Br2NS+H 414, observed 412, 414, 416.

Fuente