Ethyl formate → HCID 15023229, compound

HRID 1534530Notes

Reaction equation

HRID 1534530 reaction equation
[NH2:1][CH2:2][CH:3]1[C:12]2[C:7](=[CH:8][C:9]([O:13][CH3:14])=[CH:10][CH:11]=2)[O:6][CH2:5][CH2:4]1.[CH2:15](OC=O)C>C1(C)C=CC=CC=1>[CH3:15][NH:1][CH2:2][CH:3]1[C:12]2[C:7](=[CH:8][C:9]([O:13][CH3:14])=[CH:10][CH:11]=2)[O:6][CH2:5][CH2:4]1

Participants

4

Reactant 2

HCID 8025Ethyl formateHCID 15023228HCID 15023228, compound

Product 1

HCID 15023229HCID 15023229, compound

Reagents, catalysts & solvents 1

HCID 1140TolueneSolvent

Procedure

The product from Example 2 (5g) 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 1M THF solution) was added followed by heating for 11/2 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).

Workup

  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 1M THF solution) was added
  4. temperatureby heating for 11/2 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)

Sources & evidence

ORD record
ord-df2da9ac5fa041cfb5ef971625421949
Source dataset
uspto-grants-1992_02
Patent number
US05089519

Reaction notes

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