Potassium bisulfate → HCID 10355503, compound

HRID 1956692Notes

Reaction equation

HRID 1956692 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]([CH3:27])(=[O:26])=[O:25])[C:16](N(OC)C)=[O:17])=[O:13])([CH3:10])([CH3:9])[CH3:8].S([O-])(O)(=O)=O.[K+]>CCOCC.C1COCC1.O>[C:7]([O:11][C:12]([NH:14][C@@H:15]([CH2:22][CH2:23][S:24]([CH3:27])(=[O:26])=[O:25])[CH:16]=[O:17])=[O:13])([CH3:9])([CH3:10])[CH3:8]

Participants

7

Reactant 3

HCID 516920Potassium bisulfateHCID 10019157HCID 10019157, compoundHCID 21226445Aluminium lithium hydride

Product 1

HCID 10355503HCID 10355503, compoundYield 0%

Reagents, catalysts & solvents 3

HCID 962WaterSolventHCID 3283Diethyl EtherSolventHCID 8028TetrahydrofuranSolvent

Procedure

A suspension of lithium aluminum hydride (5.15 g, 0.136 mol) in ether (290 mL) was stirred at room temperature for one hour. The solution was cooled to -75° C. under nitrogen, and a solution of the product from Step B (23.9 g, 73.6 mol) in THF (60 mL) was added over ca. 30 min, maintaining the temperature below -40° C. When the addition was complete, the reaction was warmed to -15° C., then recooled to -35° C. A solution of potassium hydrogen sulfate (19.4 g) in 77 mL water was slowly added. The mixture was warmed to room temperature, and stirred for one hour. The solution was filtered through a pad of celite, washed with 10% HCl solution, sat. NaHCO3 solution and brine, dried (Na2 SO4), filtered, and concentrated in vacuo to provide the titled aldehyde (7.44 g).

Workup

  1. temperatureThe solution was cooled to -75° C. under nitrogen
  2. temperaturemaintaining the temperature below -40° C
  3. additionWhen the addition
  4. temperaturethe reaction was warmed to -15° C.
  5. customrecooled to -35° C
  6. temperatureThe mixture was warmed to room temperature
  7. stirringstirred for one hour
  8. filtrationThe solution was filtered through a pad of celite
  9. washwashed with 10% HCl solution, sat. NaHCO3 solution and brine
  10. customdried (Na2 SO4)
  11. filtrationfiltered
  12. concentrationconcentrated in vacuo

Sources & evidence

ORD record
ord-a159ab10c0b0432bb8966e9c60b5333c
Source dataset
uspto-grants-1998_07
Patent number
US05780492

Reaction notes

Loading…