Hydrochloric Acid → Ethyl(RS)-1-(3,4-Methylenedioxyphenyl)-3-phenylindene-2-carboxylate

HRID 863126Notes

Reaction equation

HRID 863126 reaction equation
O[C:2]1([C:22]2[CH:27]=[CH:26][C:25]3[O:28][CH2:29][O:30][C:24]=3[CH:23]=2)[C:10]2[C:5](=[CH:6][CH:7]=[CH:8][CH:9]=2)[C:4]([C:11]2[CH:16]=[CH:15][CH:14]=[CH:13][CH:12]=2)=[C:3]1[C:17]([O:19][CH2:20][CH3:21])=[O:18].C([SiH](CC)CC)C.B(F)(F)F.CCOCC.Cl>C(Cl)Cl>[CH2:29]1[O:28][C:25]2[CH:26]=[CH:27][C:22]([CH:2]3[C:10]4[C:5](=[CH:6][CH:7]=[CH:8][CH:9]=4)[C:4]([C:11]4[CH:12]=[CH:13][CH:14]=[CH:15][CH:16]=4)=[C:3]3[C:17]([O:19][CH2:20][CH3:21])=[O:18])=[CH:23][C:24]=2[O:30]1

Participants

6

Reactant 4

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

Product 1

HCID 18969642Ethyl(RS)-1-(3,4-Methylenedioxyphenyl)-3-phenylindene-2-carboxylateYield 100.8%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

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-533939d3c56e4fd2940eca6c0bcdb6c9
Source dataset
uspto-grants-1998_02
Patent number
US05719183

Reaction notes

Loading…