Ethyl formate → HCID 15023229, compound

Participants

Reaction Steps

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).

Provenance & Evidence