Boron trifluoride etherate → HCID 15125097, compound

HRID 373374Notes

Reaction equation

HRID 373374 reaction equation
[CH3:1][C:2]1[CH:7]=[C:6]([CH3:8])[C:5]([CH3:9])=[CH:4][C:3]=1[OH:10].[F:11][C:12]1[CH:17]=[CH:16][C:15]([CH:18](O)[CH2:19][CH2:20][CH2:21][CH2:22][CH2:23][C:24]([OH:26])=[O:25])=[CH:14][CH:13]=1.B(F)(F)F.CCOCC>C1(C)C=CC=CC=1>[F:11][C:12]1[CH:13]=[CH:14][C:15]([CH:18]([C:4]2[C:5]([CH3:9])=[C:6]([CH3:8])[CH:7]=[C:2]([CH3:1])[C:3]=2[OH:10])[CH2:19][CH2:20][CH2:21][CH2:22][CH2:23][C:24]([OH:26])=[O:25])=[CH:16][CH:17]=1

Participants

5

Reactant 3

HCID 8000Boron trifluoride etherateHCID 103352,4,5-TrimethylphenolHCID 145139637-(4-Fluorophenyl)-7-hydroxyheptanoic acid

Product 1

HCID 15125097HCID 15125097, compoundYield 85,488.297%

Reagents, catalysts & solvents 1

HCID 1140TolueneSolvent

Procedure

To a solution of 2,4,5-trimethylphenol (2.0 mg) and 7-(4-fluorophenyl)-7-hydroxyheptanoic acid (3.5 g) in toluene (60 ml) was added boron trifluoride ethyl ether (0.56 ml) at 70° C. and the reaction was carried out at the same temperature for 6 hours. After cooling in air, the reaction mixture was extracted by addition of water and ethyl acetate. The organic layer was washed in turn with water and saturated saline and dried with anhydrous magnesium sulfate, and the solvent was distilled off under reduced pressure. The residue was subjected to silica gel column chromatography and eluted with ethyl acetate/hexane (1 : 5) and the objective compound was recrystallized from ethyl acetate/hexane to obtain 7-(4-fluorophenyl)-7-(2-hydroxy-3,5,6-trimethylphenyl)heptanoic acid (4.5 g) (Compound 1). The physical properties and spectrum data thereof are shown in Tables 3 and 4.

Workup

  1. temperatureAfter cooling in air
  2. extractionthe reaction mixture was extracted by addition of water and ethyl acetate
  3. washThe organic layer was washed in turn with water and saturated saline
  4. dry with materialdried with anhydrous magnesium sulfate
  5. distillationthe solvent was distilled off under reduced pressure
  6. washeluted with ethyl acetate/hexane (1 : 5)
  7. customthe objective compound was recrystallized from ethyl acetate/hexane

Sources & evidence

ORD record
ord-ca472d532eb147b19b020a2e3e2a476e
Source dataset
uspto-grants-1992_11
Patent number
US05162571

Reaction notes

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