Ethanol → HCID 12919745, compound

HRID 1277949Notes

Reaction equation

HRID 1277949 reaction equation
[Br:1][C:2]1[N:12]=[CH:11][C:10]([CH:13](Br)Br)=[CH:9][C:3]=1[C:4]([O:6][CH2:7][CH3:8])=[O:5].CC[OH:18]>[N+]([O-])([O-])=O.[Ag+].O>[Br:1][C:2]1[N:12]=[CH:11][C:10]([CH:13]=[O:18])=[CH:9][C:3]=1[C:4]([O:6][CH2:7][CH3:8])=[O:5]

Participants

5

Reactant 2

HCID 702EthanolHCID 12919743HCID 12919743, compound

Product 1

HCID 12919745HCID 12919745, compoundYield 48%

Reagents, catalysts & solvents 2

HCID 24470Silver NitrateCatalystHCID 962WaterSolvent

Procedure

A mixture of 6 (9.8 g, 0.024 mol), AgNO3 (8.8 g, 0.052 mol), EtOH (100 mL) and H2O (25 mL) was heated on a steam bath for 1 hour. The yellow solid was filtered and the solution concentrated to dryness. The residue was treated with H2O and extracted with CHCl3 (3×). The organic layer was dried, filtered and concentrated to dryness. Distillation of the resulting oil at 105°-135° C. at 0.5 mm gave 3.0 g (48%) of 3; 1H NMR (CDCl3) 1.45 δ (3H, t, J=7), 4.4 (2H, q, J=7, 8.6 (1H, d, J=2),/8.9 (1H, d, J=2) and 10.1 (1H, s).

Workup

  1. temperaturewas heated on a steam bath for 1 hour
  2. filtrationThe yellow solid was filtered
  3. concentrationthe solution concentrated to dryness
  4. additionThe residue was treated with H2O
  5. extractionextracted with CHCl3 (3×)
  6. customThe organic layer was dried
  7. filtrationfiltered
  8. concentrationconcentrated to dryness
  9. distillationDistillation of the resulting oil at 105°-135° C. at 0.5 mm

Sources & evidence

ORD record
ord-a3049140d53e458683758ef10808d295
Source dataset
uspto-grants-1981_07
Patent number
US04279913

Reaction notes

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