Ammonium Hydroxide → HCID 10829892, compound

HRID 2226888Notes

Reaction equation

HRID 2226888 reaction equation
[CH3:1][CH:2]([O:4][C:5]1[C:9]2[CH:10]=[C:11]([O:14][CH2:15][C:16]3[CH:21]=[CH:20][CH:19]=[CH:18][CH:17]=3)[CH:12]=[CH:13][C:8]=2[O:7][C:6]=1[C:22]([OH:24])=O)[CH3:3].C(N1C=CN=C1)([N:27]1C=CN=C1)=O.[OH-].[NH4+]>O1CCCC1.O>[CH3:1][CH:2]([O:4][C:5]1[C:9]2[CH:10]=[C:11]([O:14][CH2:15][C:16]3[CH:21]=[CH:20][CH:19]=[CH:18][CH:17]=3)[CH:12]=[CH:13][C:8]=2[O:7][C:6]=1[C:22]([NH2:27])=[O:24])[CH3:3]

Participants

6

Reactant 3

HCID 14923Ammonium HydroxideHCID 682631,1'-CarbonyldiimidazoleHCID 10711220HCID 10711220, compound

Product 1

HCID 10829892HCID 10829892, compoundYield 53%

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 8028TetrahydrofuranSolvent

Procedure

A mixture of 3-(1-methylethoxy)-5-(phenylmethoxy)-2-benzofurancarboxylic acid (0.53 g, 1.6 mmol) and 1,1'-carbonyldiimidazole (0.29 g, 1.8 mmol) in 20 mL of tetrahydrofuran is stirred at reflux for 2 hours. The cooled reaction mixture is treated with 3.0 mL of ammonium hydroxide solution and stirred at room temperature for an additional 2 hours. The reaction mixture is diluted with water and extracted with ethyl acetate. The combined organic layers are washed with brine, dried (anhydrous magnesium sulfate), and evaporated. Purification of the residue by flash chromatography (silica gel, 50% ethyl acetate in hexane elution) gives 0.27 g (53%) of product; mp=158°-160° C.

Workup

  1. temperatureat reflux for 2 hours
  2. customThe cooled reaction mixture
  3. stirringstirred at room temperature for an additional 2 hours
  4. extractionextracted with ethyl acetate
  5. washThe combined organic layers are washed with brine
  6. dry with materialdried (anhydrous magnesium sulfate)
  7. customevaporated
  8. customPurification of the residue
  9. washby flash chromatography (silica gel, 50% ethyl acetate in hexane elution)

Sources & evidence

ORD record
ord-5575a7870f2149f19cdc7424eae82c82
Source dataset
uspto-grants-1994_09
Patent number
US05350748

Reaction notes

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