Ethyl formate → HCID 15023229, compound

The product from Example 2 (5 g) was added to ethylformate (10 ml) and toluene (100 ml) then refluxed for 21/2 hrs. The solution was evaporated to dryness and then tetrahydrofuran (THF) (100 ml) and BH3.THF 25.9 ml of a IM THF solution) was added followed by heating for 11/2 hrs. The reaction was cooled and 6N HC1 (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 21/2 hrs
2. customThe solution was evaporated to dryness
3. additiontetrahydrofuran (THF) (100 ml) and BH3.THF 25.9 ml of a IM THF solution) was added
4. temperatureby heating for 11/2 hrs
5. temperatureThe reaction was cooled
6. addition6N HC1 (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)

ORD record

ord-6682480fd09a45db9fa33b8d5646862b

Source dataset

uspto-grants-1993_02

DOI

10.6084/m9.figshare.5104873.v1

Patent number

US05185364