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

HRID 1279310Notes

Reaction equation

HRID 1279310 reaction equation
[CH2:1]1[O:9][C:8]2[CH:7]=[CH:6][C:5]([CH:10]3[C:18]4[C:13](=[CH:14][CH:15]=[CH:16][CH:17]=4)[C:12]([C:19]4[CH:24]=[CH:23][CH:22]=[CH:21][CH:20]=4)=[C:11]3[C:25]([O:27]CC)=[O:26])=[CH:4][C:3]=2[O:2]1.OC1(C2C=CC3OCOC=3C=2)C2C(=CC=CC=2)C(C2C=CC=CC=2)=C1C(OCC)=O.C([SiH](CC)CC)C.B(F)(F)F.CCOCC.Cl>C(Cl)Cl>[CH2:1]1[O:9][C:8]2[CH:7]=[CH:6][C:5]([CH:10]3[C:18]4[C:13](=[CH:14][CH:15]=[CH:16][CH:17]=4)[CH:12]([C:19]4[CH:20]=[CH:21][CH:22]=[CH:23][CH:24]=4)[CH:11]3[C:25]([OH:27])=[O:26])=[CH:4][C:3]=2[O:2]1

Participants

7

Reactant 5

HCID 313Hydrochloric AcidHCID 8000Boron trifluoride etherateHCID 12052TriethylsilaneHCID 18969642Ethyl(RS)-1-(3,4-Methylenedioxyphenyl)-3-phenylindene-2-carboxylateHCID 18969644Ethyl(1RS)-1-Hydroxy-1-(3,4-methylenedioxyphenyl)-3-phenylindene-2-carboxylate

Product 1

HCID 217147901-(3,4-Methylenedioxyphenyl)-3-phenylindane-2-carboxylic acidYield 100%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

Ethyl (RS)-1-(3,4-Methylenedioxyphenyl)-3-phenylindene-2-carboxylate. To a solution of ethyl (1RS)-1-hydroxy-1-(3,4-methylenedioxyphenyl)-3-phenylindene-2-carboxylate (1.03 g, 2.58 mmol) in CH2Cl2 (40 mL) was added triethylsilane (0.49 ml, 3.07 mmol), followed by boron trifluoride etherate (1.55 ml, 12.6 mmol). The reaction mixture was allowed to stir for 15 min, at which time was added slowly 3M HCl. The mixture was extracted with EtOAc. The organic extract was washed successively with H2O, 5% aqueous NaHCO3 and saturated aqueous NaCl. The solvent was removed in vacuo to provide the title compound (1.00 g, 100%) as a mixture of Δ1 and Δ2 double bond isomers.

Workup

  1. extractionThe mixture was extracted with EtOAc
  2. extractionThe organic extract
  3. washwas washed successively with H2O, 5% aqueous NaHCO3 and saturated aqueous NaCl
  4. customThe solvent was removed in vacuo

Sources & evidence

ORD record
ord-d0892212773541fea209a46ae9f53955
Source dataset
uspto-grants-2002_09
Patent number
US06448260B2

Reaction notes

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