Reacción #55936
ord-c5819b3f056c4e27a97e0bbb63aa7685
Ecuación de reacción
Reactantes
Reactivos
Disolventes
Condiciones de reacción
Tratamiento posterior
- 1TemperaturaAfter cooling to about 0° C.
- 2Filtraciónthe whole was filtered
- 3OtroThe filtrate was evaporated to dryness under reduced pressure
- 4workup.DISSOLUTIONthe residue (7.35 g) was dissolved in about 100 ml tetrahydrofuran
- 5workup.STIRRINGThe whole was then stirred for about 16 hours at room temperature
- 6FiltraciónAfter filtering
- 7Otrothe filtrate was evaporated to dryness under reduced pressure
- 8FiltraciónThe residue was filtered through about 100 g silica gel with hexane/acetone 9:1 by weight (500 ml)
Procedimiento
A solution of about 9.20 g (24.6 mmol) dl-3-methyl-2-[6-(m-methoxy-phenyl)-2-hydroxy-3-hexynyl]-2-cyclopentenone ethylene dithioketal in 53 ml tetrahydrofuran was added dropwise over a period of about 20 minutes to a suspension of 1.86 g (49 mmol) lithium aluminium hydride in about 80 ml tetrahydrofuran under a nitrogen atmosphere. The mixture was stirred in a water-bath at about 60° C. for about 4 hours. After cooling to about 0° C., the following consecutive dropwise additions were cautiously made to the suspension: 1.86 ml water, 1.86 ml 15% sodium hydroxide solution and 5.50 ml water. Sodium sulphate (5 g) was added and the whole was filtered. The filtrate was evaporated to dryness under reduced pressure and the residue (7.35 g) was dissolved in about 100 ml tetrahydrofuran. The following consecutive additions were made to this solution under nitrogen: 20.0 g (370 mmol) powdered potassium hydroxide and 20.0 ml (214 mmol) benzyl chloride. The whole was then stirred for about 16 hours at room temperature. After filtering, the filtrate was evaporated to dryness under reduced pressure. The residue was filtered through about 100 g silica gel with hexane/acetone 9:1 by weight (500 ml) giving 8.70 g product.