Sodium Sulfate → HCID 58238575, compound

HRID 45479Notes

Reaction equation

HRID 45479 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:23]=[C:24]([C:28]2[CH:33]=[CH:32][CH:31]=[CH:30][C:29]=2[O:34][CH3:35])[CH:25]=[CH:26][CH:27]=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:23]=[C:24]([C:28]2[CH:33]=[CH:32][CH:31]=[CH:30][C:29]=2[O:34][CH3:35])[CH:25]=[CH:26][CH:27]=1)[CH3:21])([CH3:8])[CH3:9]

Participants

5

Reactant 3

HCID 24436Sodium SulfateHCID 21226445Aluminium lithium hydrideHCID 58238573(2,6-Diisopropylphenyl)[1-(2'-methoxybiphenyl-3-yl)ethylidene]amine

Product 1

HCID 58238575HCID 58238575, compound

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

To a suspension of 0.70 g (18.4 mmol) of LiAlH4 in 60 mL of THF, 2.25 g (5.84 mmol) of 39 was added. This reaction mixture was refluxed for 2 hr, and then saturated aqueous Na2SO4 was added. The organic layer was separated, and the aqueous layer was extracted with 2×50 mL of diethyl ether. The combined organic extract was evaporated to dryness, and the product was isolated by flash chromatography on silica gel 60 (40-63 um, eluent: hexanes-diethyl ether from 100:1 to 20:1, vol.) to yield 1.45 g (64%) of Fl.

Workup

  1. additionwas added
  2. temperatureThis reaction mixture was refluxed for 2 hr
  3. customThe organic layer was separated
  4. extractionthe aqueous layer was extracted with 2×50 mL of diethyl ether
  5. extractionThe combined organic extract
  6. customwas evaporated to dryness
  7. customthe product was isolated by flash chromatography on silica gel 60 (40-63 um, eluent: hexanes-diethyl ether from 100:1 to 20:1, vol.)
  8. customto yield 1.45 g (64%) of Fl

Sources & evidence

ORD record
ord-9aa044796f2a4b589cf199da4ec90909
Source dataset
uspto-grants-2013_09
Patent number
US08541522B2

Reaction notes

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