Reacción #2355682

Ecuación de reacción

triethylamine

oxalyl chloride

dimethylsulfoxide

8-(4,5,6,7-tetramethoxy-2-phenylindan-2-yl)octanol

→

compound

Rendimiento 99.0%

8-(4,5,6,7-Tetramethoxy-2-phenylindan-2-yl)octanal

Rendimiento 99.0%

Disolventes

THF

THF

water

THF

Condiciones de reacción

Tratamiento posterior

1. 1
   workup.STIRRINGAfter being stirred for 15 min
2. 2
   workup.ADDITIONwas dropwise added
3. 3
   workup.STIRRINGstirred for 20 min
4. 4
   Extracciónextracted with ethyl acetate
5. 5
   LavadoThe organic layer was washed with water and saturated aqueous sodium chloride
6. 6
   Otrodried
7. 7
   OtroThe solvent was removed in vacuo
8. 8
   OtroThe residue was purified by silica gel column chromatography (hexane to hexane:ethyl acetate=4:1)

Procedimiento

To a solution of oxalyl chloride (0.394 ml) in THF (36 ml) was dropwise added a solution of dimethylsulfoxide (468 mg) in THF (2.4 ml) at −70° C. or under nitrogen atmosphere. After the reaction mixture was stirred for 10 min, a solution of 8-(4,5,6,7-tetramethoxy-2-phenylindan-2-yl)octanol (1.00 g) in THF (12 ml) was dropwise added to the reaction mixture at −70° C. or under. After being stirred for 15 min, the reaction mixture was stirred at between −60° C. and −50° C. for 1 hr, to which triethylamine (2.30 ml) was dropwise added. The reaction mixture was allowed to warm to 0° C. and stirred for 20 min, diluted with water, and extracted with ethyl acetate. The organic layer was washed with water and saturated aqueous sodium chloride and dried. The solvent was removed in vacuo. The residue was purified by silica gel column chromatography (hexane to hexane:ethyl acetate=4:1) to yield the entitled compound (985 mg) as an oil.

Fuente