Sodium Hydroxide → HCID 9868726, compound

HRID 1017890Notes

Reaction equation

HRID 1017890 reaction equation
[Cl-].[Al+3].[Cl-].[Cl-].[H-].[Al+3].[Li+].[H-].[H-].[H-].[CH:11]([C:14]1[CH:19]=[CH:18][C:17]([CH:20]2[C:24]3[C:25]([CH3:43])=[C:26]([NH:31][C:32]([C:34]4[CH:42]=[CH:41][C:37]5[O:38][CH2:39][O:40][C:36]=5[CH:35]=4)=O)[C:27]([CH3:30])=[C:28]([CH3:29])[C:23]=3[O:22][C:21]2([CH3:45])[CH3:44])=[CH:16][CH:15]=1)([CH3:13])[CH3:12].[OH-].[Na+]>O1CCCC1>[O:38]1[C:37]2[CH:41]=[CH:42][C:34]([CH2:32][NH:31][C:26]3[C:27]([CH3:30])=[C:28]([CH3:29])[C:23]4[O:22][C:21]([CH3:45])([CH3:44])[CH:20]([C:17]5[CH:16]=[CH:15][C:14]([CH:11]([CH3:13])[CH3:12])=[CH:19][CH:18]=5)[C:24]=4[C:25]=3[CH3:43])=[CH:35][C:36]=2[O:40][CH2:39]1

Participants

6

Reactant 4

HCID 14798Sodium HydroxideHCID 6451240Aluminum(III) ChlorideHCID 10183771HCID 10183771, compoundHCID 21226445Aluminium lithium hydride

Product 1

HCID 9868726HCID 9868726, compoundYield 40%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

To a suspension of aluminum chloride (847 mg, 6.35 mmol) in tetrahydrofuran (10 ml) was gradually added under ice cooling lithium aluminum hydride (240 mg, 6.35 mmol) and the resulting mixture was stirred at the same temperature for 10 minutes. To this mixture was added N-[3-(4-isopropylphenyl)-2,2,4,6,7-pentamethyl-2,3-dihydro-1-benzofuran-5-yl]-1,3-benzodioxol-5-carboxamide (0.60 g, 1.27 mmol) and the mixture was refluxed with heating for 3 hours. The reaction mixture was poured into ice water and neutralized with an 8 N aqueous solution of sodium hydroxide. The product was extracted twice with ethyl acetate. The combined organic layers were washed with water, dried on magnesium sulfate, filtered, and then concentrated under reduced pressure. The residue was crystallized from methanol to obtain 0.23 g (40% yield) of the title compound. Melting point: 100-102° C.

Workup

  1. additionwas gradually added under ice
  2. temperaturethe mixture was refluxed
  3. temperaturewith heating for 3 hours
  4. extractionThe product was extracted twice with ethyl acetate
  5. washThe combined organic layers were washed with water
  6. customdried on magnesium sulfate
  7. filtrationfiltered
  8. concentrationconcentrated under reduced pressure
  9. customThe residue was crystallized from methanol

Sources & evidence

ORD record
ord-01796a344cae4bea9683642d6aa6cacd
Source dataset
uspto-grants-2002_11
Patent number
US06479536B1

Reaction notes

Loading…