Ammonium Chloride → Ethylacetate heptane

HRID 2377206Notes

Reaction equation

HRID 2377206 reaction equation
[C:1]([C:5]1C=[C:7](C(=O)/C=C/C2C=CC(C(O)=O)=CC=2)[CH:8]=[C:9](C2C=CC(C)=CC=2)[C:10]=1[O:11][CH2:12][CH:13](C)C)(C)(C)[CH3:2].[OH2:36].O.O.O.O.O.O.[Cl-].[Ce+3].[Cl-].[Cl-].[BH4-].[Na+].[Cl-].[NH4+]>CO>[CH3:2][CH2:1][CH2:5][CH2:10][CH2:9][CH2:8][CH3:7].[C:10]([O:11][CH2:12][CH3:13])(=[O:36])[CH3:5]

Participants

6

Reactant 4

HCID 25517Ammonium ChlorideHCID 4311764Sodium borohydrideHCID 120848254-[(E)-3-(5-tert-Butyl-6-isobutoxy-4'-methyl-3-biphenylyl)-3-oxopropenyl]benzoic AcidHCID 21585214Cerium trichloride heptahydrate

Product 1

HCID 21899848Ethylacetate heptaneYield 212.4%

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Procedure

440 mg (0.9 mmol) of 4-[(E)-3-(5-tert-butyl-6-isobutoxy-4′-methyl-3-biphenylyl)-3-oxopropenyl]benzoic acid are dissolved in 50 mL of methanol. 450 mg (1.2 mmol) of cerium chloride heptahydrate are added, and the medium is stirred for 30 minutes. 70 mg (1.9 mmol) of sodium borohydride are then added, and the reaction medium is stirred for 15 minutes until completely decolorized, and then treated with a saturated ammonium chloride solution. The residue obtained after extraction with ethyl acetate is purified by chromatography (eluent: 1 heptane/1 ethyl acetate). A white crystalline solid is obtained after recrystallization from a heptane/ethyl acetate mixture (m=180 mg; yield=42%; m.p.=175° C.).

Workup

  1. stirringthe reaction medium is stirred for 15 minutes
  2. customThe residue obtained
  3. extractionafter extraction with ethyl acetate
  4. customis purified by chromatography (eluent: 1 heptane/1 ethyl acetate)
  5. customA white crystalline solid is obtained

Sources & evidence

ORD record
ord-686088ddba774de086e5ca9b0baf0d00
Source dataset
uspto-grants-2008_12
Patent number
US07468457B2

Reaction notes

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