Hydrochloric Acid → 1-(4-Methoxyphenyl)-3-phenylindane-2-carboxylic acid

HRID 1279294Notes

Reaction equation

HRID 1279294 reaction equation
[CH3:1][O:2][C:3]1[CH:8]=[CH:7][C:6]([CH:9]2[C:17]3[C:12](=[CH:13][CH:14]=[CH:15][CH:16]=3)[C:11]([C:18]3[CH:23]=[CH:22][CH:21]=[CH:20][CH:19]=3)=[C:10]2[C:24]([O:26]CC)=[O:25])=[CH:5][CH:4]=1.C([SiH](CC)CC)C.B(F)(F)F.CCOCC.Cl>C(Cl)Cl>[CH3:1][O:2][C:3]1[CH:8]=[CH:7][C:6]([CH:9]2[C:17]3[C:12](=[CH:13][CH:14]=[CH:15][CH:16]=3)[CH:11]([C:18]3[CH:19]=[CH:20][CH:21]=[CH:22][CH:23]=3)[CH:10]2[C:24]([OH:26])=[O:25])=[CH:5][CH:4]=1

Participants

6

Reactant 4

HCID 313Hydrochloric AcidHCID 8000Boron trifluoride etherateHCID 12052TriethylsilaneHCID 18969659ethyl (RS)-I-(4methoxyphenyl)-3-phenylindene-2-carboxylate

Product 1

HCID 159084991-(4-Methoxyphenyl)-3-phenylindane-2-carboxylic acidYield 95%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

Ethyl (RS)-1-(4-Methoxyphenyl)-3-phenylindene-2-carboxylate. To a solution of ethyl (1RS) [1-hydroxy-1-(4-methoxyphenyl)]-3-phenylindene-2-carboxylate (4.65 g, 12.0 mmol) in CH2Cl2 (40 ml) at 0° C. under an argon atmosphere was added triethylsilane (2.34 ml, 14.6 mmol), followed by boron trifluoride etherate (8.8 ml, 71 mmol). The reaction mixture was allowed to warm to room temperature and stirred for 10 min, at which time was added slowly 3M HCl (50 ml). The mixture was extracted with EtOAc (150 ml). The organic extract was washed successively with H2O, aqueous NaHCO3, H2O and saturated aqueous NaCl and dried. The solvent was removed in vacuo, and the residue was purified by flash chromatography on silica gel, eluting with 10% EtOAc/ hexanes to provide the title compound (4.2 g, 95%) as a mixture of Δ1 and Δ2 double bond isomers.

Workup

  1. extractionThe mixture was extracted with EtOAc (150 ml)
  2. extractionThe organic extract
  3. washwas washed successively with H2O, aqueous NaHCO3, H2O and saturated aqueous NaCl
  4. customdried
  5. customThe solvent was removed in vacuo
  6. customthe residue was purified by flash chromatography on silica gel
  7. washeluting with 10% EtOAc/ hexanes

Sources & evidence

ORD record
ord-c98bc2eb576d468d87015f7c092286cf
Source dataset
uspto-grants-2002_09
Patent number
US06448260B2

Reaction notes

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