Reacción #7942

Ecuación de reacción

4-bromo-2-butyl-5-methoxy-1-indanone

LiCl

PPh3

Me4Sn

→

2-butyl-5-methoxy-4-methyl-1-indanone

Disolventes

water

dimethylformamide

Condiciones de reacción

Tratamiento posterior

1. 1
   TemperaturaAfter cooling to room temperature
2. 2
   Extracciónextracted with Et2O (100 mL, 2×25 mL)
3. 3
   LavadoThe ether extracts were washed with brine
4. 4
   Secadodried over MgSO4
5. 5
   Filtraciónfiltered
6. 6
   Otroevaporated under vacuum to a yellow solid (1.29 g)
7. 7
   OtroThis material was purified by chromatography on EM silica gel 60 (230-400 mesh, 130 mL dry, packed under CH2Cl2)
8. 8
   Lavadoas eluting solvent

Procedimiento

A solution of 4-bromo-2-butyl-5-methoxy-1-indanone (1.159 g, 3.90 mmol) in anhydrous dimethylformamide (39 mL) was treated with LiCl (455 mg, 10.73 mmol), PPh3 (205 mg, 0.78 mmol), PdCl2(PPh3)2 (205 mg, 0.292 mmol) and Me4Sn (1.08 mL, 7.80 mmol). The mixture was placed under a nitrogen atmosphere, then stirred and heated in an oil bath at 100° C. for 16.5 hours. After cooling to room temperature, the mixture was diluted with water (100 mL) and extracted with Et2O (100 mL, 2×25 mL). The ether extracts were washed with brine, dried over MgSO4, filtered and evaporated under vacuum to a yellow solid (1.29 g). This material was purified by chromatography on EM silica gel 60 (230-400 mesh, 130 mL dry, packed under CH2Cl2), using CH2Cl2 as eluting solvent, to afford a 92:3:5 mixture (0.90 g) of 2-butyl-5-methoxy-4-methyl-1-indanone, the 6-methyl isomer, and the desmethyl product. This material was used as is in the next step.

Fuente