Hydrochloric Acid → HCID 68987514, compound

HRID 2249617Notes

Reaction equation

HRID 2249617 reaction equation
[CH2:1]([O:5][C:6]1[CH:29]=[C:28]([O:30][CH2:31][CH:32]([CH3:34])[CH3:33])[CH:27]=[CH:26][C:7]=1[C:8]([C:10]1[CH:11]=[CH:12][C:13]([O:21][CH2:22][CH:23]([CH3:25])[CH3:24])=[C:14]([CH:16]=[CH:17][C:18]([OH:20])=[O:19])[CH:15]=1)=[O:9])[CH:2]([CH3:4])[CH3:3].[H-].[Al+3].[Li+].[H-].[H-].[H-].C(Cl)(Cl)Cl.Cl>O1CCCC1.O>[CH2:1]([O:5][C:6]1[CH:29]=[C:28]([O:30][CH2:31][CH:32]([CH3:34])[CH3:33])[CH:27]=[CH:26][C:7]=1[CH:8]([OH:9])[C:10]1[CH:11]=[CH:12][C:13]([O:21][CH2:22][CH:23]([CH3:25])[CH3:24])=[C:14]([CH:16]=[CH:17][C:18]([OH:20])=[O:19])[CH:15]=1)[CH:2]([CH3:4])[CH3:3]

Participants

7

Reactant 4

HCID 313Hydrochloric AcidHCID 6212ChloroformHCID 21226445Aluminium lithium hydrideHCID 69220068HCID 69220068, compound

Product 1

HCID 68987514HCID 68987514, compoundYield 53.1%

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 8028TetrahydrofuranSolvent

Procedure

In 2 ml of tetrahydrofuran is dissolved 150 mg of 3-[5-(2,4-diisobutoxybenzoyl)-2-isobutoxyphenyl]-2-propenoic acid. After adding 14 mg of lithium aluminum hydride at 5-10° C., the mixture thus obtained is stirred for one hour. The reaction mixture is added to a mixture of chloroform and water, pH is adjusted to 3.0 with 2 mol/L hydrochloric acid, and the organic layer is separated. After successively washing the organic layer with water and saturated aqueous solution of sodium chloride and drying it over anhydrous magnesium sulfate, the solvent is distilled off under reduced pressure. The residue thus obtained is purified by silica gel column chromatography [eluent; n-hexane:ethyl acetate=4:1] to obtain 80 mg of 3-[5-[(2,4-diisobutoxyphenyl)(hydroxy)methyl]-2-isobutoxyphenyl]-2-propenoic acid as a colorless foaming product.

Workup

  1. customthe mixture thus obtained
  2. customthe organic layer is separated
  3. washAfter successively washing the organic layer with water and saturated aqueous solution of sodium chloride
  4. dry with materialdrying it over anhydrous magnesium sulfate
  5. distillationthe solvent is distilled off under reduced pressure
  6. customThe residue thus obtained
  7. customis purified by silica gel column chromatography [eluent; n-hexane:ethyl acetate=4:1]

Sources & evidence

ORD record
ord-c2e8bf5ba6254a3f92866d40c63399bc
Source dataset
uspto-grants-2008_01
Patent number
US07314888B1

Reaction notes

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