Reacción #362925

Ecuación de reacción

Ethylene oxide

Butyl lithium

6-methoxybenzo[b]thiophene

HCl

→

6-methoxybenzo[b]thiophene-2-ethanol

Disolventes

tetrahydrofuran

Condiciones de reacción

Tratamiento posterior

1. 1
   Otroprepared analogous to the procedure
2. 2
   Temperaturato warm to room temperature
3. 3
   workup.STIRRINGstirred for 3 hours
4. 4
   OtroThe solvent was evaporated
5. 5
   workup.ADDITIONThe residue was diluted with water
6. 6
   Extracciónthis mixture was extracted with CH2Cl2
7. 7
   OtroThe separated organic layer was dried
8. 8
   Filtraciónfiltered
9. 9
   Otrothe solvent evaporated
10. 10
    workup.STIRRINGThe residue was stirred in hexane
11. 11
    Filtraciónfiltered off
12. 12
    Otrodried

Procedimiento

Butyl lithium (0.27 mol of a 2.5 M solution) was added dropwise to 6-methoxybenzo[b]thiophene [prepared analogous to the procedure described in J. Med. Chem. 1989, 32(12), 2548-2554] (0.25 mol) in tetrahydrofuran (1000 ml), stirred at −30° C. The mixture was stirred for 10 minutes at −30° C. Ethylene oxide (0.38 mol in 100 ml tetrahydrofuran) was added dropwise at −30° C. The mixture was allowed to warm to room temperature and stirred for 3 hours. The mixture was acidified with dilute HCl solution. The solvent was evaporated. The residue was diluted with water and this mixture was extracted with CH2Cl2. The separated organic layer was dried, filtered and the solvent evaporated. The residue was stirred in hexane, filtered off and dried, yielding 41.3 g of 6-methoxybenzo[b]thiophene-2-ethanol (interm. 2).

Fuente