Acetone → HCID 18696591, compound

HRID 1870534Notes

Reaction equation

HRID 1870534 reaction equation
[CH3:1][O:2][C:3]1[N:7]([C:8]2[CH:12]=[CH:11][S:10][C:9]=2[C:13](OC)=[O:14])[C:6](=[O:17])[N:5]([CH3:18])[N:4]=1.[H-].C([Al+]CC(C)C)C(C)C.CC(C)=O>C(Cl)Cl>[OH:14][CH2:13][C:9]1[S:10][CH:11]=[CH:12][C:8]=1[N:7]1[C:3]([O:2][CH3:1])=[N:4][N:5]([CH3:18])[C:6]1=[O:17]

Participants

5

Reactant 3

HCID 180AcetoneHCID 18696615HCID 18696615, compoundHCID 21225700Diisobutylaluminumhydride

Product 1

HCID 18696591HCID 18696591, compoundYield 80.6%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent2×

Conditions

Temperature
-78 °C

Procedure

To a solution of the title compound of Step D (1.8 g) in methylene chloride (23 mL) under N2 at -78° C. was added a solution of diisobutylaluminum hydride (18.3 mL, 1 M) in methylene chloride. The resulting solution was allowed to stir at -78° C. for 15 min, warmed to room temperature and then stirred for 1.5 h. After cooling the reaction mixture to -78° C., acetone was added and after about 10 min, the reaction mixture was quenched with 1N HCl. The reaction mixture was allowed to warm to room temperature, was diluted further with methylene chloride, and was then washed with water. The organic layer was dried (MgSO4), filtered and concentrated in vacuo to yield 1.3 g of the title compound of Step E as an off-white solid.

Workup

  1. temperaturewarmed to room temperature
  2. stirringstirred for 1.5 h
  3. temperatureAfter cooling the reaction mixture to -78° C.
  4. customthe reaction mixture was quenched with 1N HCl
  5. temperatureto warm to room temperature
  6. additionwas diluted further with methylene chloride
  7. washwas then washed with water
  8. dry with materialThe organic layer was dried (MgSO4)
  9. filtrationfiltered
  10. concentrationconcentrated in vacuo

Sources & evidence

ORD record
ord-38f9fad35a96498ca3c9232479c52cf2
Source dataset
uspto-grants-2000_08
Patent number
US06096895

Reaction notes

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