Potassium bisulfate → HCID 22941134, compound

HRID 342100Notes

Reaction equation

HRID 342100 reaction equation
CON(C)[C:4]([C@@H:6]1[CH2:8][C@H:7]1[C:9]1[C:14]2[CH2:15][CH2:16][O:17][C:13]=2[CH:12]=[CH:11][CH:10]=1)=[O:5].[H-].[H-].[H-].[H-].[Li+].[Al+3].S([O-])(O)(=O)=O.[K+]>C1COCC1.O>[O:17]1[C:13]2[CH:12]=[CH:11][CH:10]=[C:9]([C@@H:7]3[CH2:8][C@H:6]3[CH:4]=[O:5])[C:14]=2[CH2:15][CH2:16]1

Participants

6

Reactant 3

HCID 516920Potassium bisulfateHCID 21226445Aluminium lithium hydrideHCID 22941145HCID 22941145, compound

Product 1

HCID 22941134HCID 22941134, compoundYield 99%

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 8028TetrahydrofuranSolvent2×

Conditions

Temperature
5 °C

Procedure

A solution of (±)-(trans)-N-methoxy-N-methyl-2-(2,3-dihydrobenzofuran-4-yl)cyclopropanecarboxamide (3.7 g, 15 mmol) in THF (10 mL) was added dropwise to a rapidly stirred suspension of LAH (683 mg, 18 mmol) in THF (50 mL) at -45° C., maintaining the temperature below -40° C. throughout. The cooling bath was removed, the reaction was allowed to warm to 5° C., and then the reaction was immediately recooled to -45° C. Potassium hydrogen sulfate (3.4 g, 25.5 mmol) in H2O (50 mL) was cautiously added dropwise, the temperature maintained below -30° C. throughout. The cooling bath was removed and the suspension was stirred at room temperature for 30 min. The mixture was filtered through Celite and the filter cake was washed with ether. The combined filtrates were then washed with cold 1N HCl, 1N NaOH, and brine. The filtrates were dried over MgSO4, and concentrated in vacuo to give a clear oil (2.6 g, 99%).

Workup

  1. temperaturemaintaining the temperature below -40° C. throughout
  2. customThe cooling bath was removed
  3. customwas immediately recooled to -45° C
  4. temperaturethe temperature maintained below -30° C. throughout
  5. customThe cooling bath was removed
  6. filtrationThe mixture was filtered through Celite
  7. washthe filter cake was washed with ether
  8. washThe combined filtrates were then washed with cold 1N HCl, 1N NaOH, and brine
  9. dry with materialThe filtrates were dried over MgSO4
  10. concentrationconcentrated in vacuo

Sources & evidence

ORD record
ord-88701143365649fe9212bd276e316252
Source dataset
uspto-grants-1999_01
Patent number
US05856529

Reaction notes

Loading…