Hydrochloric Acid → HCID 68514453, compound

HRID 1876936Notes

Reaction equation

HRID 1876936 reaction equation
[CH2:1]([C:3]1[O:4][C:5]([C:20]2[CH:25]=[CH:24][C:23]([C:26]([F:29])([F:28])[F:27])=[CH:22][CH:21]=2)=[CH:6][C:7]=1[CH2:8][O:9][C:10]1[CH:19]=[CH:18][C:13]([C:14]([O:16]C)=[O:15])=[CH:12][CH:11]=1)[CH3:2].[OH-].[Na+].O.Cl>CO.O1CCCC1>[CH2:1]([C:3]1[O:4][C:5]([C:20]2[CH:21]=[CH:22][C:23]([C:26]([F:29])([F:27])[F:28])=[CH:24][CH:25]=2)=[CH:6][C:7]=1[CH2:8][O:9][C:10]1[CH:11]=[CH:12][C:13]([C:14]([OH:16])=[O:15])=[CH:18][CH:19]=1)[CH3:2]

Participants

7

Reactant 4

HCID 313Hydrochloric AcidHCID 962WaterHCID 14798Sodium HydroxideHCID 68513506HCID 68513506, compound

Product 1

HCID 68514453HCID 68514453, compoundYield 86%

Reagents, catalysts & solvents 2

HCID 887MethanolSolventHCID 8028TetrahydrofuranSolvent

Conditions

Temperature
60 °C

Procedure

To a solution of {2-ethyl-5-[4-(trifluoromethyl)phenyl]-3-furyl}methanol (324 mg) obtained by the above-mentioned reaction and methyl 4-hydroxybenzoate (228 mg) in tetrahydrofuran (10 mL) were added tributylphosphine (0.6 mL) and 1,1′-(azodicarbonyl)dipiperidine (606 mg), and the mixture was stirred at room temperature overnight. The solvent was evaporated under reduced pressure, and the residue was purified by silica gel column (0% ethyl acetate/hexane to 15% ethyl acetate/hexane) to give methyl 4-({2-ethyl-5-[4-(trifluoromethyl)phenyl]-3-furyl}methoxy)benzoate as a white solid. The obtained methyl 4-({2-ethyl-5-[4-(trifluoromethyl)phenyl]-3-furyl}methoxy)benzoate was dissolved in methanol (5 mL) and tetrahydrofuran (5 mL), 2N sodium hydroxide (2.0 mL) were added, and the mixture was stirred at 60° C. for 2 hr. The reaction mixture was poured into water, and the mixture was acidified with 1N hydrochloric acid and extracted with ethyl acetate. The organic layer was washed with saturated brine, and dried over magnesium sulfate. The solvent was evaporated under reduced pressure, and the residue was crystallized from ethyl acetate/hexane to give the title compound (236 mg, 86%).

Workup

  1. extractionextracted with ethyl acetate
  2. washThe organic layer was washed with saturated brine
  3. dry with materialdried over magnesium sulfate
  4. customThe solvent was evaporated under reduced pressure
  5. customthe residue was crystallized from ethyl acetate/hexane

Sources & evidence

ORD record
ord-be077611b2224e88871cf97a12ec13f2
Source dataset
uspto-grants-2012_11
Patent number
US08309580B2

Reaction notes

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