반응 #362925

반응 방정식

Ethylene oxide

Butyl lithium

6-methoxybenzo[b]thiophene

HCl

→

6-methoxybenzo[b]thiophene-2-ethanol

용매

tetrahydrofuran

반응 조건

후처리

1. 1
   기타prepared analogous to the procedure
2. 2
   온도to warm to room temperature
3. 3
   workup.STIRRINGstirred for 3 hours
4. 4
   기타The solvent was evaporated
5. 5
   workup.ADDITIONThe residue was diluted with water
6. 6
   추출this mixture was extracted with CH2Cl2
7. 7
   기타The separated organic layer was dried
8. 8
   여과filtered
9. 9
   기타the solvent evaporated
10. 10
    workup.STIRRINGThe residue was stirred in hexane
11. 11
    여과filtered off
12. 12
    기타dried

실험 절차

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).

출처