Hydrochloric Acid → HCID 10786648, compound

HRID 1755951Notes

Reaction equation

HRID 1755951 reaction equation
[CH3:1][O:2][CH:3]([CH2:6][C:7]1[CH:8]=[CH:9][C:10]2[O:14][C:13]([CH2:15][C:16]3[N:17]=[C:18]([C:22]4[CH:27]=[CH:26][CH:25]=[CH:24][CH:23]=4)[O:19][C:20]=3[CH3:21])=[CH:12][C:11]=2[CH:28]=1)[C:4]#N.C(O)C.[OH-:32].[Na+].Cl.[OH2:35]>>[CH3:1][O:2][CH:3]([CH2:6][C:7]1[CH:8]=[CH:9][C:10]2[O:14][C:13]([CH2:15][C:16]3[N:17]=[C:18]([C:22]4[CH:27]=[CH:26][CH:25]=[CH:24][CH:23]=4)[O:19][C:20]=3[CH3:21])=[CH:12][C:11]=2[CH:28]=1)[C:4]([OH:35])=[O:32]

Participants

6

Reactant 5

HCID 313Hydrochloric AcidHCID 702EthanolHCID 962WaterHCID 14798Sodium HydroxideHCID 10690653HCID 10690653, compound

Product 1

HCID 10786648HCID 10786648, compound

Procedure

A mixture of 2-methoxy-3-[2-((5-methyl-2-phenyl-4-oxazolyl) methyl)benzofuran-5-yl]propanenitrile (0.64 g, 1.7 mmol), ethanol (30 ml) and 6N sodium hydroxide (10 ml) was heated to reflux for 3 hours. Water (30 ml) was added and the solution was acidified with concentrated hydrochloric acid (6 ml), then extracted with ethyl acetate (2 x) . The combined organic layers were washed with brine, dried over magnesium sulfate and concentrated. The product was recrystallized from ethyl acetate/hexanes and obtained as a white solid (0.47 g, mp 159°-160.5° C.).

Workup

  1. temperaturewas heated
  2. temperatureto reflux for 3 hours
  3. extractionextracted with ethyl acetate (2 x)
  4. washThe combined organic layers were washed with brine
  5. dry with materialdried over magnesium sulfate
  6. concentrationconcentrated
  7. customThe product was recrystallized from ethyl acetate/hexanes

Sources & evidence

ORD record
ord-bab4ab5dfda5470ab2ec46519447c117
Source dataset
uspto-grants-1995_08
Patent number
US05438074

Reaction notes

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