Acetic Acid → HCID 21916256, compound

HRID 1349412Notes

Reaction equation

HRID 1349412 reaction equation
[CH2:1]([C:3]1[N:4]=[C:5]2[N:9]([C:10]3[C:15]([CH3:16])=[CH:14][C:13]([CH3:17])=[CH:12][C:11]=3[CH3:18])[CH2:8][CH2:7][N:6]2[C:19]=1[C:20]([CH2:24][CH2:25][CH3:26])=[CH:21][CH2:22][CH3:23])[CH3:2].B.C1COCC1.C(O)(=O)C.CO>O1CCCC1>[CH2:1]([C:3]1[N:4]=[C:5]2[N:9]([C:10]3[C:11]([CH3:18])=[CH:12][C:13]([CH3:17])=[CH:14][C:15]=3[CH3:16])[CH2:8][CH2:7][N:6]2[C:19]=1[CH:20]([CH2:21][CH2:22][CH3:23])[CH2:24][CH2:25][CH3:26])[CH3:2]

Participants

6

Reactant 4

HCID 176Acetic AcidHCID 887MethanolHCID 2723981Borane;tetrahydrofuranHCID 69422345HCID 69422345, compound

Product 1

HCID 21916256HCID 21916256, compound

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Conditions

Temperature
0 °C

Procedure

6-Ethyl-5-(1-propyl-but-1-enyl)-1-(2,4,6-trimethyl-phenyl)-2,3-dihydro-1H-imidazo[1,2-a]imidazole (0.013 g, 0.000037 mol) in anhydrous tetrahydrofuran was treated with cold BH3-THF (0.15 mL 1.0 M in tetrahydrofuran), and the mixture was heated at reflux for 1.5 h. The mixture was cooled to 0° C., treated with glacial acetic acid (0.25 mL), heated at reflux for 1.5 h, re-cooled to 0° C., treated with 1.5 mL methanol, and heated again at reflux for 1 h. Upon cooling to room temperature, the reaction mixture was concentrated under reduced pressure, and the residue was partitioned between 2.5 N NaOH and ether. The organic phase was washed with water and brine, and was then dried over anhydrous Na2SO4 and evaporated to give a pale yellow oil. The crude product was chromatographed on silica, eluting with 15% ethyl acetate/hexanes to give a glassy solid. LC/MS: tR=1.81 min., (MH+)=354.30.

Workup

  1. temperaturethe mixture was heated
  2. temperatureat reflux for 1.5 h
  3. temperatureheated
  4. temperatureat reflux for 1.5 h
  5. temperaturere-cooled to 0° C.
  6. temperatureheated again
  7. temperatureat reflux for 1 h
  8. temperatureUpon cooling to room temperature
  9. concentrationthe reaction mixture was concentrated under reduced pressure
  10. customthe residue was partitioned between 2.5 N NaOH and ether
  11. washThe organic phase was washed with water and brine
  12. dry with materialwas then dried over anhydrous Na2SO4
  13. customevaporated
  14. customto give a pale yellow oil
  15. customThe crude product was chromatographed on silica
  16. washeluting with 15% ethyl acetate/hexanes
  17. customto give a glassy solid

Sources & evidence

ORD record
ord-04c901a7614c4da39fa3d29f61f731a7
Source dataset
uspto-grants-2007_05
Patent number
US07211669B2

Reaction notes

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