Ammonium → HCID 53729251, compound

HRID 2387741Notes

Reaction equation

HRID 2387741 reaction equation
[H-].[Al+3].[Li+].[H-].[H-].[H-].[F:7][C:8]1[CH:9]=[CH:10][C:11]([O:18][CH2:19][O:20][CH3:21])=[C:12]([CH:17]=1)[C:13](OC)=[O:14].[NH4+].S([O-])([O-])(=O)=O.[Mg+2]>C1COCC1>[F:7][C:8]1[CH:9]=[CH:10][C:11]([O:18][CH2:19][O:20][CH3:21])=[C:12]([CH2:13][OH:14])[CH:17]=1

Participants

6

Reactant 4

HCID 223AmmoniumHCID 24083Sulfuric acid magnesium salt (1:1)HCID 10867629HCID 10867629, compoundHCID 21226445Aluminium lithium hydride2×

Product 1

HCID 53729251HCID 53729251, compoundYield 48.5%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

Lithium aluminum hydride (2.2 g) was added to a THF (200 ml) solution of the compound 324-1 (12.4 g), while the solution was stirred under cooling on ice. The obtained mixture was stirred at room temperature for 3 hours. Ice was added by portions to the reaction solution, and thereby excessive lithium aluminum hydride was decomposed. Thereafter, a small amount of 27% ammonium aqueous solution and Celite were added to the residue, and the obtained mixture was stirred at room temperature for 20 minutes. Magnesium sulfate was added to the reaction solution, and the mixture was filtered. The filtrate was concentrated under reduced pressure. The obtained residue was purified by silica gel column chromatography (n-heptane/ethyl acetate=1:0 to 3:1), so as to obtain the title compound (5.23 g).

Workup

  1. temperatureunder cooling on ice
  2. stirringThe obtained mixture was stirred at room temperature for 3 hours
  3. additionIce was added by portions to the reaction solution
  4. stirringthe obtained mixture was stirred at room temperature for 20 minutes
  5. filtrationthe mixture was filtered
  6. concentrationThe filtrate was concentrated under reduced pressure
  7. customThe obtained residue was purified by silica gel column chromatography (n-heptane/ethyl acetate=1:0 to 3:1)

Sources & evidence

ORD record
ord-a7770ce7dc6e48118010868f51a992ae
Source dataset
uspto-grants-2012_09
Patent number
US08268848B2

Reaction notes

Loading…