반응 #8899

반응 방정식

product

Methyl 5-(4-chlorophenyl)-6-(2,4-dichlorophenyl)-2-(3,4-difluorophenyl)-3-oxo-2,3-dihydrofuro[2,3-b]pyridine-2-carboxylate

sodium borohydride

→

title compound

5-(4-Chlorophenyl)-6-(2,4-dichlorophenyl)-2-(3,4-difluorophenyl)-furo[2,3-b]pyridin-3-ol

용매

EtOH

반응 조건

후처리

1. 1
   기타then partitioned between EtOAc and water
2. 2
   기타The organic layer was separated
3. 3
   건조dried (MgSO4)
4. 4
   여과filtered
5. 5
   기타evaporated
6. 6
   workup.DISSOLUTIONThe residue was then redissolved in 10 mL MeOH
7. 7
   workup.ADDITION2 mL of a 2.0 N solution of sodium hydroxide was added
8. 8
   workup.STIRRINGThe reaction mixture was stirred at 80° C. for 0.5 h
9. 9
   온도cooled to room temperature
10. 10
    기타partitioned between EtOAc and 10% aq. NaHSO4
11. 11
    기타The organic layer was separated
12. 12
    세척washed with water
13. 13
    건조dried (MgSO4)
14. 14
    여과filtered
15. 15
    기타evaporated
16. 16
    기타The residue was purified on a silica gel flash chromatography column
17. 17
    세척eluted with 0–20% EtOAc-hexane
18. 18
    기타Combination of the purified fractions and drying in vacuo

실험 절차

To a solution of 80 mg (0.14 mmol) of the product of Step B dissolved in 1 mL EtOH was added 9 mg (0.20 mmol) of sodium borohydride. The reaction mixture was stirred at RT for 5 min then partitioned between EtOAc and water. The organic layer was separated, dried (MgSO4), filtered and evaporated. The residue was then redissolved in 10 mL MeOH and 2 mL of a 2.0 N solution of sodium hydroxide was added. The reaction mixture was stirred at 80° C. for 0.5 h, then cooled to room temperature and partitioned between EtOAc and 10% aq. NaHSO4. The organic layer was separated, washed with water, dried (MgSO4), filtered and evaporated. The residue was purified on a silica gel flash chromatography column eluted with 0–20% EtOAc-hexane. Combination of the purified fractions and drying in vacuo afforded the title compound.

출처