Hydrochloric Acid → HCID 66896657, compound

HRID 1394642Notes

Reaction equation

HRID 1394642 reaction equation
C[O:2][C:3](=[O:31])[CH:4]=[C:5]([C:7]1[CH:8]=[CH:9][C:10]2[O:14][N:13]=[C:12]([C:15]3[CH:20]=[C:19]([CH:21]([CH3:23])[CH3:22])[CH:18]=[C:17]([CH:24]([CH3:26])[CH3:25])[C:16]=3[O:27][CH2:28][CH3:29])[C:11]=2[CH:30]=1)[CH3:6].Cl>CO.[OH-].[Na+]>[CH2:28]([O:27][C:16]1[C:17]([CH:24]([CH3:26])[CH3:25])=[CH:18][C:19]([CH:21]([CH3:22])[CH3:23])=[CH:20][C:15]=1[C:12]1[C:11]2[CH:30]=[C:7]([C:5]([CH3:6])=[CH:4][C:3]([OH:31])=[O:2])[CH:8]=[CH:9][C:10]=2[O:14][N:13]=1)[CH3:29]

Participants

5

Reactant 2

HCID 313Hydrochloric AcidHCID 69217716HCID 69217716, compound

Product 1

HCID 66896657HCID 66896657, compound

Reagents, catalysts & solvents 2

HCID 887MethanolSolventHCID 14798Sodium HydroxideSolvent

Procedure

A solution of 3-[3-(2-ethoxy-3,5-diisopropyl-phenyl)-benzo[d]isoxazol-5-yl]-but-2-enoic acid methyl ester (99.6 mg, 0.24 mmol) in 2 mL of methanol and 2 ml of 1N NaOH solution was heated this mixture to 60° C. for 3 h, then cooled and brought to pH 2 with 1N HCl. The reaction mixture was extracted with ethyl acetate (2×10 mL), and the organic layers were dried over MgSO4 and evaporated to a residue. The residue was purified by silica gel chromatography (50% ethyl acetate in hexanes) to give a clear oil, which solidified upon standing to a waxy solid (12.1 mg, 13%).

Workup

  1. temperaturecooled
  2. extractionThe reaction mixture was extracted with ethyl acetate (2×10 mL)
  3. dry with materialthe organic layers were dried over MgSO4
  4. customevaporated to a residue
  5. customThe residue was purified by silica gel chromatography (50% ethyl acetate in hexanes)
  6. customto give a clear oil, which

Sources & evidence

ORD record
ord-7ae667b074ed4f6c9c768d53bbed9836
Source dataset
uspto-grants-2008_03
Patent number
US07348359B2

Reaction notes

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