Sodium Sulfate → HCID 58238564, compound

HRID 45450Notes

Reaction equation

HRID 45450 reaction equation
[H-].[H-].[H-].[H-].[Li+].[Al+3].[CH:7]([C:10]1[CH:15]=[CH:14][CH:13]=[C:12]([CH:16]([CH3:18])[CH3:17])[C:11]=1/[N:19]=[C:20](\[C:22]1[CH:27]=[CH:26][CH:25]=[C:24]([C:28]2[CH:33]=[CH:32][CH:31]=[CH:30][N:29]=2)[CH:23]=1)/[CH3:21])([CH3:9])[CH3:8].[O-]S([O-])(=O)=O.[Na+].[Na+]>C1COCC1>[CH:7]([C:10]1[CH:15]=[CH:14][CH:13]=[C:12]([CH:16]([CH3:18])[CH3:17])[C:11]=1[NH:19][CH:20]([C:22]1[CH:27]=[CH:26][CH:25]=[C:24]([C:28]2[CH:33]=[CH:32][CH:31]=[CH:30][N:29]=2)[CH:23]=1)[CH3:21])([CH3:8])[CH3:9]

Participants

5

Reactant 3

HCID 24436Sodium SulfateHCID 21226445Aluminium lithium hydrideHCID 178463284HCID 178463284, compound

Product 1

HCID 58238564HCID 58238564, compoundYield 91%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

To a suspension of 2.70 g (71.0 mmol) of LiAlH4 in 250 mL of THF, 8.03 g (22.6 mmol) of 14 was added. This mixture was refluxed for 3 hr, and then saturated aqueous Na2SO4 was added. The organic layer was separated, and the aqueous layer was additionally washed with 2×100 ml, of diethyl ether. The combined organic extract was evaporated to dryness, and the product was isolated using flash chromatography on silica gel 60 (40-63 um, eluent: hexanes-diethyl ether from 100:1 to 10:1, vol.) to yield 7.37 g (91%) of C1.

Workup

  1. additionwas added
  2. temperatureThis mixture was refluxed for 3 hr
  3. customThe organic layer was separated
  4. washthe aqueous layer was additionally washed with 2×100 ml, of diethyl ether
  5. extractionThe combined organic extract
  6. customwas evaporated to dryness
  7. customthe product was isolated

Sources & evidence

ORD record
ord-d5398858e2f94205a4435f9f10217dad
Source dataset
uspto-grants-2013_09
Patent number
US08541522B2

Reaction notes

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