Tetrahydrofuran → HCID 22993353, compound

HRID 1167621Notes

Reaction equation

HRID 1167621 reaction equation
[CH3:1][O:2][C:3]1[CH:4]=[CH:5][C:6]2[O:11][CH:10]([C:12]3[CH:17]=[CH:16][CH:15]=[CH:14][CH:13]=3)[C:9](=O)[NH:8][C:7]=2[CH:19]=1.O1CCCC1.[H-].[Al+3].[Li+].[H-].[H-].[H-].[OH-].[Na+]>O>[CH3:1][O:2][C:3]1[CH:4]=[CH:5][C:6]2[O:11][CH:10]([C:12]3[CH:17]=[CH:16][CH:15]=[CH:14][CH:13]=3)[CH2:9][NH:8][C:7]=2[CH:19]=1

Participants

6

Reactant 4

HCID 8028TetrahydrofuranHCID 14798Sodium HydroxideHCID 21226445Aluminium lithium hydrideHCID 22993363HCID 22993363, compound

Product 1

HCID 22993353HCID 22993353, compound

Reagents, catalysts & solvents 1

HCID 962WaterSolvent2×

Procedure

Under an inert atmosphere, the compound obtained in Step B (3.26 g; 12.77 mmol) is dissolved in 70 ml of anhydrous tetrahydrofuran (6 ml/1 mmol), and then lithium aluminium hydride (5 eq.; 63.85 mmol; 2.42 g) is added in portions at 0° C. The mixture is stirred at ambient temperature for 16 hours, and then the solution is hydrolysed at 0° C. with 2.4 ml of water, 2.4 ml of a 15% sodium hydroxide solution and 7.2 ml of water. The solution is stirred for 30 minutes, and the salts that have formed are filtered off using a Büchner funnel and the solvent is removed under reduced pressure. The crude reaction product is purified by flash chromatography on silica gel (eluant: PE/AcOEt (8/2)). The title product is obtained in the form of a solid.

Workup

  1. stirringThe solution is stirred for 30 minutes
  2. customthe salts that have formed
  3. filtrationare filtered off
  4. customthe solvent is removed under reduced pressure
  5. customThe crude reaction product
  6. customis purified by flash chromatography on silica gel (eluant: PE/AcOEt (8/2))

Sources & evidence

ORD record
ord-7243c222eee64ab3a5503f94031f05cc
Source dataset
uspto-grants-2003_09
Patent number
US06620809B2

Reaction notes

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