Sodium Sulfate → HCID 58238549, compound

HRID 45435Notes

Reaction equation

HRID 45435 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:37]1[CH:42]=[CH:41][CH:40]=[CH:39][CH:38]=1)/[C:21]1[CH:26]=[C:25]([CH3:27])[CH:24]=[C:23]([C:28]2[CH:33]=[CH:32][CH:31]=[CH:30][C:29]=2[O:34][CH3:35])[C:22]=1[OH:36])([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]([CH3:17])[CH3:18])[C:11]=1[NH:19][CH:20]([C:37]1[CH:38]=[CH:39][CH:40]=[CH:41][CH:42]=1)[C:21]1[CH:26]=[C:25]([CH3:27])[CH:24]=[C:23]([C:28]2[CH:33]=[CH:32][CH:31]=[CH:30][C:29]=2[O:34][CH3:35])[C:22]=1[OH:36])([CH3:8])[CH3:9]

Participants

5

Reactant 3

HCID 24436Sodium SulfateHCID 21226445Aluminium lithium hydrideHCID 178489288HCID 178489288, compound

Product 1

HCID 58238549HCID 58238549, compoundYield 64.2%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

To a suspension of 0.34 g (8.0 mmol) of LiAlH4 in 25 mL of THF, 1.19 g (2.50 mmol) of 35 was added. The obtained mixture was stirred for 4 hr, and then a saturated aqueous solution of Na2SO4 was added. The organic layer was separated, and the aqueous layer was washed by 2×50 mL of diethyl ether. The combined organic extract was evaporated to dryness. The product was isolated by flash-chromatography on silica gel 60 (40-63 um, eluent: from hexanes to hexanes-diethyl ether, 20:1, vol.) to yield 0.77 g (64%) of the title product.

Workup

  1. additionwas added
  2. customThe organic layer was separated
  3. washthe aqueous layer was washed by 2×50 mL of diethyl ether
  4. extractionThe combined organic extract
  5. customwas evaporated to dryness
  6. customThe product was isolated by flash-chromatography on silica gel 60 (40-63 um, eluent: from hexanes to hexanes-diethyl ether, 20:1, vol.)

Sources & evidence

ORD record
ord-4fb7fca05294429b807745a8602b9214
Source dataset
uspto-grants-2013_09
Patent number
US08541521B2

Reaction notes

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