Sodium Hydroxide → HCID 9868726, compound

HRID 272380Notes

Reaction equation

HRID 272380 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-e4c4ee3f02704f04b6e7f1d8eb9f1830
Source dataset
uspto-grants-2008_11
Patent number
US07456162B2

Reaction notes

Loading…