Potassium bisulfate → HCID 45092115, compound

HRID 1956685Notes

Reaction equation

HRID 1956685 reaction equation
[H-].[Al+3].[Li+].[H-].[H-].[H-].[C:7]([O:11][C:12]([NH:14][CH:15]([CH2:22][C:23]#[C: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][CH:15]([CH2:22][C:23]#[C:24][CH3:25])[CH:16]=[O:17])=[O:13])([CH3:10])([CH3:9])[CH3:8]

Participants

6

Reactant 3

HCID 516920Potassium bisulfateHCID 21226445Aluminium lithium hydrideHCID 21258867Carbamic acid, [1-[(methoxymethylamino)carbonyl]-3-pentynyl]-, 1,1-dimethylethyl ester

Product 1

HCID 45092115HCID 45092115, compound

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 3283Diethyl EtherSolvent2×

Procedure

A suspension of lithium aluminum hydride (1.56 g, 41.1 mmol) in ether (150 mL) was stirred at room temperature for 30 minutes. The solution was cooled to -55° C. under nitrogen, and a solution of the product from Step J (11.10 g, 41.1 mmol) in ether (150 mL) was added over 15 min, maintaining the temperature below -50° C. When the addition was complete, the reaction was warmed to 5° C., then recooled to -40° C. A solution of potassium hydrogen sulfate (21.8 g) in 25 mL water was slowly added, maintaining the temperature below -35° C. The mixture was warmed to room temperature and stirred for one hour, filtered through Celite, and concentrated in vacuo to provide the title aldehyde.

Workup

  1. temperatureThe solution was cooled to -55° C. under nitrogen
  2. temperaturemaintaining the temperature below -50° C
  3. additionWhen the addition
  4. temperaturethe reaction was warmed to 5° C.
  5. customrecooled to -40° C
  6. temperaturemaintaining the temperature below -35° C
  7. temperatureThe mixture was warmed to room temperature
  8. stirringstirred for one hour
  9. filtrationfiltered through Celite
  10. concentrationconcentrated in vacuo

Sources & evidence

ORD record
ord-41bcdf6c8f63496e8b439867b782e0bb
Source dataset
uspto-grants-1998_07
Patent number
US05780492

Reaction notes

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