反应详情

The product from Example 2 (5g) was added to ethylformate (10 ml) and toluene (100 ml) then refluxed for 2 1/2 hrs. The solution was evaporated to dryness and then tetrahydrofuran (THF) (100 ml) and BH3. THF (25.9 ml of a 1M THF solution) was added followed by heating for 1 1/2 hrs. The reaction was cooled and 6N HCl (20 ml) was carefully added followed by heating for 1 hr. The THF was evaporated and the reaction made basic with aqueous KOH. The reaction was extracted with CH2Cl2, the organic layer then separated, dried (MgSO4), filtered and evaporated. The residue was chromatographed on silica gel and eluted with (EtOAc:H2O:HCO2H) (16:2:2), giving the product (1.4 g). Mass spec: (M+H)+ 208. 1H NMR(CDCl3): 2.0 (m,2H); 2.49 (s,3H); 2.8 (m,2H); 3.75 (s,3H); 4.2 (m.1H); 6.38-7.25 (m,3H).

1. temperaturethen refluxed for 2 1/2 hrs
2. customThe solution was evaporated to dryness
3. additionTHF (25.9 ml of a 1M THF solution) was added
4. temperatureby heating for 1 1/2 hrs
5. temperatureThe reaction was cooled
6. addition6N HCl (20 ml) was carefully added
7. temperatureby heating for 1 hr
8. customThe THF was evaporated
9. extractionThe reaction was extracted with CH2Cl2
10. customthe organic layer then separated
11. dry with materialdried (MgSO4)
12. filtrationfiltered
13. customevaporated
14. customThe residue was chromatographed on silica gel
15. washeluted with (EtOAc:H2O:HCO2H) (16:2:2)