Hexane → HCID 86761435, compound

HRID 555657Notes

Reaction equation

HRID 555657 reaction equation
C[O:2][C:3]([C:5]1[O:9][C:8]([C:10]2[C:11]3[CH:23]=[CH:22][Se:21][C:12]=3[N:13]([C:15]3[CH:20]=[CH:19][CH:18]=[CH:17][CH:16]=3)[N:14]=2)=[CH:7][CH:6]=1)=O.C(OCC)(=O)C.CCCCCC>O>[OH:2][CH2:3][C:5]1[O:9][C:8]([C:10]2[C:11]3[CH:23]=[CH:22][Se:21][C:12]=3[N:13]([C:15]3[CH:20]=[CH:19][CH:18]=[CH:17][CH:16]=3)[N:14]=2)=[CH:7][CH:6]=1

Participants

5

Reactant 3

HCID 8058HexaneHCID 8857Ethyl AcetateHCID 54588370HCID 54588370, compound

Product 1

HCID 86761435HCID 86761435, compoundYield 88.9%

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Procedure

1.98 g (0.018 mole) of granular anhydrous calcium chloride, 1.377 g (0.036 mole) of sodium brorhydride and 100 ml of anhydrous THF were reacted at room temperature for 4 h to form a white dispersion of calcium borohydride (Ca(BH4)2). To the dispersion compound 78 (0.744 g, 0.002 mole) was added and was reduced by heating under refluxing for 24 h. The progress of the reduction reaction was monitored by TLC with ethyl acetate (EA):n-hexane=3:2. When the reaction was completed, the reaction mixture was cooled to room temperature, and THF was evaporated under a reduced pressure. The remaining reaction mixture was poured into water to stop the reaction, and then was extracted with chloroform. The organic layer was recovered, dried over MgSO4 and filtered. The solvent of the filtrate was evaporated under a reduced pressure, and the residue was subjected to a column chromatography with EA:n-hexane=3:2, and then recrystallized from EA to afford compound 80 in white crystals (0.612 g). Yield: 88.9%;

Workup

  1. temperatureby heating
  2. temperatureunder refluxing for 24 h
  3. customThe progress of the reduction reaction
  4. customTHF was evaporated under a reduced pressure
  5. customThe remaining reaction mixture
  6. customthe reaction
  7. extractionwas extracted with chloroform
  8. customThe organic layer was recovered
  9. dry with materialdried over MgSO4
  10. filtrationfiltered
  11. customThe solvent of the filtrate was evaporated under a reduced pressure
  12. customn-hexane=3:2, and then recrystallized from EA

Sources & evidence

ORD record
ord-23ed90458c67492c978a695063a54c9c
Source dataset
uspto-grants-2011_11
Patent number
US08053459B1

Reaction notes

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