Boron trifluoride etherate → HCID 10539699, compound

HRID 485602Notes

Reaction equation

HRID 485602 reaction equation
[C:1]1([C:9]2[CH:14]=[CH:13][CH:12]=[CH:11][CH:10]=2)[C:2](C=O)=[CH:3][CH:4]=[CH:5][CH:6]=1.[Br-].[C:16]([CH2:19][CH2:20][CH2:21][CH2:22][CH2:23]P(C1C=CC=CC=1)(C1C=CC=CC=1)C1C=CC=CC=1)([OH:18])=[O:17].C([O-])([O-])=O.[K+].[K+].C1OCCOCCOCCOCCOCCOC1.B(F)(F)F.CCOCC>O1CCCC1.O>[C:9]1([C:1]2[CH:6]=[CH:5][C:4](/[CH:23]=[CH:22]/[CH2:21][CH2:20][CH2:19][C:16]([OH:18])=[O:17])=[CH:3][CH:2]=2)[CH:10]=[CH:11][CH:12]=[CH:13][CH:14]=1

Participants

8

Reactant 5

HCID 8000Boron trifluoride etherateHCID 11430Potassium CarbonateHCID 2855718-Crown-6HCID 121052(1,1'-Biphenyl)-2-carboxaldehydeHCID 178525449HCID 178525449, compound

Product 1

HCID 10539699HCID 10539699, compoundYield 59%

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 8028TetrahydrofuranSolvent

Procedure

Six grams biphenylcarboxaldehyde, 10.23 g 5-carboxypentyl triphenylphosphorane bromide, 5.8 g anhydrous K2CO3 and 130 mg 18-Crown-6 were suspended in 240 mL dry tetrahydrofuran. The mixture was heated and stirred at reflux for 7 days, diluted with 200 mL H2O, extracted with EtOAc (5×200 mL). The EtOAc extract was dried (Na2SO4) and concentrated, the residue was taken up in methanol (200 mL) treated with 1 equivalent BF3.OEt2 and the methyl esters of the cis and trans acids separated by chromatography (yield 59%). The esters were hydrolyzed upon dissolving in MeOH (100 mL) and treatment with 1N NaOH (50 mL). Acidification resulted in precipitation of the corresponding acids cis-6-(4'-biphenyl)hex-5-enoic acid, m.p. 107°-109° and trans-6-(4'-biphenylyl)hex-5-enoic acid, m.p. 116°-118°.

Workup

  1. temperatureThe mixture was heated
  2. temperatureat reflux for 7 days
  3. extractionextracted with EtOAc (5×200 mL)
  4. extractionThe EtOAc extract
  5. dry with materialwas dried (Na2SO4)
  6. concentrationconcentrated
  7. customthe methyl esters of the cis and trans acids separated by chromatography (yield 59%)
  8. dissolutionupon dissolving in MeOH (100 mL)

Sources & evidence

ORD record
ord-904acf58d85b4e7aa5d037281cd9d012
Source dataset
uspto-grants-1985_08
Patent number
US04536515

Reaction notes

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