Potassium bisulfate → HCID 13245620, compound

HRID 342135Notes

Reaction equation

HRID 342135 reaction equation
[H-].[Al+3].[Li+].[H-].[H-].[H-].[C:7]([O:11][C:12]([NH:14][C@@H:15]([CH2:22][CH2:23][S:24][CH3:25])[C:16](N(OC)C)=[O:17])=[O:13])([CH3:10])([CH3:9])[CH3:8].S([O-])(O)(=O)=O.[K+]>CCOCC.O>[C:7]([O:11][C:12]([NH:14][C@@H:15]([CH2:22][CH2:23][S:24][CH3:25])[CH:16]=[O:17])=[O:13])([CH3:10])([CH3:9])[CH3:8]

Participants

6

Reactant 3

HCID 516920Potassium bisulfateHCID 11779122HCID 11779122, compoundHCID 21226445Aluminium lithium hydride

Product 1

HCID 13245620HCID 13245620, compound

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 3283Diethyl EtherSolvent2×

Procedure

A suspension of lithium aluminum hydride (5.02 g, 0.132 mol) in ether (500 mL) was stirred at room temperature for one hour. The solution was cooled to -50° C. under nitrogen, and a solution of the product from Step F (39.8 g, ca. 0.120 mol) in ether (200 mL) was added over 30 min, maintaining the temperature below -40° C. When the addition was complete, the reaction was warmed to 5° C., then recooled to -45° C. Analysis by tic revealed incomplete reaction. The solution was rewarmed to 5° C., stirred for 30 minutes, then cooled to -50° C. A solution of potassium hydrogen sulfate (72 g, 0.529 mol) in 200 mL water was slowly added, maintaining the temperature below -20° C. The mixture was warmed to 5° C. filtered through Celite, and concentrated in vacuo to provide the title aldehyde.

Workup

  1. temperatureThe solution was cooled to -50° C. under nitrogen
  2. temperaturemaintaining the temperature below -40° C
  3. additionWhen the addition
  4. temperaturethe reaction was warmed to 5° C.
  5. customrecooled to -45° C
  6. customreaction
  7. customwas rewarmed to 5° C.
  8. stirringstirred for 30 minutes
  9. temperaturecooled to -50° C
  10. temperaturemaintaining the temperature below -20° C
  11. temperatureThe mixture was warmed to 5° C.
  12. filtrationfiltered through Celite
  13. concentrationconcentrated in vacuo

Sources & evidence

ORD record
ord-9b21ed5d597f43e58d0642f2843d9c77
Source dataset
uspto-grants-1999_01
Patent number
US05856326

Reaction notes

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