Hydrochloric Acid → HCID 10786648, compound

HRID 1464809Notes

Reaction equation

HRID 1464809 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×). 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×)
  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-3eddef46c6c8466ea9783e490611ef79
Source dataset
uspto-grants-1994_04
Patent number
US05306726

Reaction notes

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