Reacción #2293765

Ecuación de reacción

ethyl 2-methyl-2-(2-methyl-1H-indol-1-yl)propanoate

lithium aluminum hydride

→

2-methyl-2-(2-methyl-1H-indol-1-yl)propan-1-ol

Rendimiento 79.0%

Disolventes

tetrahydrofuran

tetrahydrofuran

Condiciones de reacción

Tratamiento posterior

1. 1
   workup.ADDITIONAfter the addition
2. 2
   workup.STIRRINGto stir for 3 hours at room temperature
3. 3
   Otroquenched by 10 mL water
4. 4
   FiltraciónThe resulting white precipitate was filtered off
5. 5
   Lavadowashed with acetic ester
6. 6
   SecadoThe filtrate was dried by anhydrous sodium sulphate
7. 7
   OtroThe solvent was removed
8. 8
   Otroto afford the crude product
9. 9
   Otroan purified by column chromatograph on silica gel
10. 10
    Lavadoeluted with (petrol ether/acetic ester 20:1→10:1→5:1)

Procedimiento

To a solution of ethyl 2-methyl-2-(2-methyl-1H-indol-1-yl)propanoate (1.2 g, 4.9 mmol) in anhydrous tetrahydrofuran (10 mL) was added lithium aluminum hydride (1 g, 24.5 mmol) dissolved in anhydrous tetrahydrofuran (5 mL) dropwise between −10° C. and 0° C. After the addition, the mixture was stirred below 0° C. for 1 hour, and then allowed to stir for 3 hours at room temperature. The reaction mixture was cooled down to 0° C., quenched by 10 mL water, and then 10 mL 4N sodium hydroxide. The resulting white precipitate was filtered off, washed with acetic ester. The filtrate was dried by anhydrous sodium sulphate. The solvent was removed to afford the crude product an purified by column chromatograph on silica gel eluted with (petrol ether/acetic ester 20:1→10:1→5:1) to give 2-methyl-2-(2-methyl-1H-indol-1-yl)propan-1-ol (780 mg, 79%) as a light green oil. LCMS (M+H+) m/z: calcd. 202.14. found 202.9.

Fuente