Ethyl Acetate → HCID 10709629, compound

HRID 1464803Notes

Reaction equation

HRID 1464803 reaction equation
[CH3:1][C:2]1[O:6][C:5]([C:7]2[CH:12]=[CH:11][CH:10]=[CH:9][CH:8]=2)=[N:4][C:3]=1[CH:13]([C:15]1[O:16][CH:17]=[C:18]2[CH:23]=[C:22]([N+:24]([O-])=O)[CH:21]=[CH:20][C:19]=12)O.C([SiH](CC)CC)C.C(OCC)(=O)C>FC(F)(F)C(O)=O.[Pt]=O>[NH2:24][C:22]1[CH:23]=[CH:18][C:17]2[O:16][C:15]([CH2:13][C:3]3[N:4]=[C:5]([C:7]4[CH:12]=[CH:11][CH:10]=[CH:9][CH:8]=4)[O:6][C:2]=3[CH3:1])=[CH:19][C:20]=2[CH:21]=1

Participants

6

Reactant 3

HCID 8857Ethyl AcetateHCID 12052TriethylsilaneHCID 67696857HCID 67696857, compound

Product 1

HCID 10709629HCID 10709629, compound

Reagents, catalysts & solvents 2

HCID 82844Platinum oxide (PtO)CatalystHCID 6422Trifluoroacetic acidSolvent

Conditions

Temperature
0 °C

Procedure

alpha-(5-Methyl-2-phenyl-4-oxazolyl)-5-nitro-2-benzofuranmethanol (57 g, 0.16 mol) was dissolved in trifluoroacetic acid (350 ml), while cooling to 0° C. Triethylsilane (64 ml, 0.40 mol) was added. The solution was stirred 1.5 hours at 0° C. and overnight at room temperature. The solution was concentrated to near-dryness and the residue dissolved in ethyl acetate (750 ml). This solution was washed with water. The precipitate formed during the wash was collected. The organic solution was washed with satured sodium bicarbonate, during which more precipitate formed and was collected. The ethyl acetate phase of the filtrate was washed again with saturated sodium bicarbonate, then with brine, dried over sodium sulfate and concentrated. The residue was triturated with isopropyl ether and a solid was obtained. The combined solids obtained hereabove (51 g, 0.15 mol) were placed in a Parr bottle together with platinum oxide (3 g) and ethyl acetate (1.5 1) and hydrogenated at 40 psi for 1.25 hours. The catalyst was filtered through Celite, and after washing the filtering pad with more ethyl acetate, the solvent was removed in vacuo to give a yellow residue which was triturated with isopropyl ether (200 ml). The pale yellow solid was collected (37.1 g, mp 161.5°-162.5° C).

Workup

  1. concentrationThe solution was concentrated to near-dryness
  2. dissolutionthe residue dissolved in ethyl acetate (750 ml)
  3. washThis solution was washed with water
  4. customThe precipitate formed during the wash
  5. customwas collected
  6. washThe organic solution was washed with satured sodium bicarbonate, during which
  7. custommore precipitate formed
  8. customwas collected
  9. washThe ethyl acetate phase of the filtrate was washed again with saturated sodium bicarbonate
  10. dry with materialwith brine, dried over sodium sulfate
  11. concentrationconcentrated
  12. customThe residue was triturated with isopropyl ether
  13. customa solid was obtained
  14. customThe combined solids obtained hereabove (51 g, 0.15 mol)
  15. filtrationThe catalyst was filtered through Celite
  16. washafter washing the filtering pad with more ethyl acetate
  17. customthe solvent was removed in vacuo
  18. customto give a yellow residue which
  19. customwas triturated with isopropyl ether (200 ml)
  20. customThe pale yellow solid was collected (37.1 g, mp 161.5°-162.5° C)

Sources & evidence

ORD record
ord-9e632d8b4ae34ec783ccffaca501c834
Source dataset
uspto-grants-1994_04
Patent number
US05306726

Reaction notes

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