Boron trifluoride etherate → (1RS,3RS)-1,3-Di-(3,4-methylenedioxyphenyl)indane-2-carboxylic acid

HRID 2288151Notes

Reaction equation

HRID 2288151 reaction equation
C1OC2C=CC(C3C4C(=CC=CC=4)C=C3C([O-])=O)=CC=2O1.[CH2:22]1[O:30][C:29]2[CH:28]=[CH:27][C:26]([C:31]3(O)[C:39]4[C:34](=[CH:35][CH:36]=[CH:37][CH:38]=4)[C:33]([C:40]4[CH:45]=[CH:44][C:43]5[O:46][CH2:47][O:48][C:42]=5[CH:41]=4)=[C:32]3[C:49]([O:51]CC)=[O:50])=[CH:25][C:24]=2[O:23]1.C([SiH](CC)CC)C.B(F)(F)F.CCOCC>C(Cl)Cl>[CH2:22]1[O:30][C:29]2[CH:28]=[CH:27][C:26]([CH:31]3[C:39]4[C:34](=[CH:35][CH:36]=[CH:37][CH:38]=4)[CH:33]([C:40]4[CH:45]=[CH:44][C:43]5[O:46][CH2:47][O:48][C:42]=5[CH:41]=4)[CH:32]3[C:49]([OH:51])=[O:50])=[CH:25][C:24]=2[O:23]1

Participants

6

Reactant 4

HCID 8000Boron trifluoride etherateHCID 12052TriethylsilaneHCID 21714787Ethyl (1RS)-1,3-di-(3,4-methylenedioxyphenyl)-1-hydroxyindene-2-carboxylateHCID 86755511HCID 86755511, compound

Product 1

HCID 10135727(1RS,3RS)-1,3-Di-(3,4-methylenedioxyphenyl)indane-2-carboxylic acidYield 98.3%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

Ethyl (RS)-1,3-Di-(3,4-methylenedioxyphenylindene-2-carboxylate. To a solution of ethyl (1RS)-1,3-di-(3,4-methylenedioxyphenyl)-1-hydroxyindene-2-carboxylate (0.29 g, 0.65 mmol) in CH2Cl2 (3 ml) at 0° C. under an argon atmosphere was added triethylsilane (91 mg, 0.78 mmol), followed by boron trifluoride etherate (0.3 ml, 2.4 mmnol). The reaction mixture was stirred for 10 min, at which time was added ice-cold 1 M HCl, and the mixture was extracted with EtOAc. The organic extract was washed with saturated aqueous NaCl and dried (MgSO4). The solvent was removed in vacuo, and the residue was placed on a small pad of silica gel, eluting with CH2Cl2 to provide the title compound (257 mg, 92%).

Workup

  1. extractionthe mixture was extracted with EtOAc
  2. extractionThe organic extract
  3. washwas washed with saturated aqueous NaCl
  4. dry with materialdried (MgSO4)
  5. customThe solvent was removed in vacuo
  6. washeluting with CH2Cl2

Sources & evidence

ORD record
ord-dfebbf90e2d3420cae921576c05c2a80
Source dataset
uspto-grants-2000_07
Patent number
US06087389

Reaction notes

Loading…