Sodium Sulfate → HCID 58238555, compound

HRID 45430Notes

Reaction equation

HRID 45430 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]=[C:26]([CH3:28])[CH:25]=[C:24]([C:29]2[CH:34]=[CH:33][CH:32]=[CH:31][C:30]=2[O:35][CH3:36])[C:23]=1[OH:37])\[CH3:21])([CH3:9])[CH3:8].[O-]S([O-])(=O)=O.[Na+].[Na+]>C1COCC1>[CH:16]([C:12]1[CH:13]=[CH:14][CH:15]=[C:10]([CH:7]([CH3:9])[CH3:8])[C:11]=1[NH:19][CH:20]([C:22]1[CH:27]=[C:26]([CH3:28])[CH:25]=[C:24]([C:29]2[CH:34]=[CH:33][CH:32]=[CH:31][C:30]=2[O:35][CH3:36])[C:23]=1[OH:37])[CH3:21])([CH3:17])[CH3:18]

Participants

5

Reactant 3

HCID 24436Sodium SulfateHCID 21226445Aluminium lithium hydrideHCID 178489287HCID 178489287, compound

Product 1

HCID 58238555HCID 58238555, compoundYield 82.4%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

To a suspension of 0.34 g (8.0 mmol) of LiAlH4 in 25 mL of THF, 1.04 g (2.50 mmol) of 31 was added. The obtained mixture was stirred for 4 hr, and then saturated aqueous solution of Na2SO4 was added. The organic layer was separated, and the aqueous layer was washed with 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-ether, 20:1, vol.) to give 0.86 g (82%) of F1.

Workup

  1. additionwas added
  2. customThe organic layer was separated
  3. washthe aqueous layer was washed with 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-ether, 20:1, vol.)

Sources & evidence

ORD record
ord-c9148fb05eb0411cbcde99e42bf1276b
Source dataset
uspto-grants-2013_09
Patent number
US08541521B2

Reaction notes

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