Lithium Chloride → HCID 86752132, compound

HRID 399241Notes

Reaction equation

HRID 399241 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]=[C:15]([O:18][CH2:19][CH2:20][CH3:21])[CH:16]=3)[CH:11]([C:22]3[CH:27]=[CH:26][C:25]4[O:28][CH2:29][O:30][C:24]=4[CH:23]=3)[CH:10]2[C:31]([O:33][CH3:34])=[O:32])=[C:5](OS(C(F)(F)F)(=O)=O)[CH:4]=1.[Cl-].[Li+]>CN(C)C=O>[CH2:8]([C:5]1[CH:4]=[C:3]([O:2][CH3:1])[CH:8]=[CH:7][C:6]=1[CH:9]1[C:17]2[C:12](=[CH:13][CH:14]=[C:15]([O:18][CH2:19][CH2:20][CH3:21])[CH:16]=2)[CH:11]([C:22]2[CH:27]=[CH:26][C:25]3[O:28][CH2:29][O:30][C:24]=3[CH:23]=2)[CH:10]1[C:31]([O:33][CH3:34])=[O:32])[CH2:3][CH2:4][CH3:5]

Participants

4

Reactant 2

HCID 433294Lithium ChlorideHCID 18969658HCID 18969658, compound

Product 1

HCID 86752132HCID 86752132, compoundYield 77.4%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

Methyl(1RS,2SR,3RS)-3-(4-methoxy-2-trifluoromethanesulfonyloxyphenyl)-1-(3,4-methylenedioxyphenyl)-5-(prop-1-yloxy)indane-2-carboxylate (0.118 g, 0.19 mmol), lithium chloride (0.058 g, 1.37 mmol), tetrakis(tri-phenylphosphine)palladium(0) (0.018 g, 0.016 mmol) and ethyl 3-[tri-(butyl-1-yl)stannyl]benzoate (0.253 g, 0.58 mmol) were mixed in dry dimethylformamide (5 ml) and refluxed for 24 h. The product was filtered through celite and the celite washed with ethyl acetate. The combined filtrate was evaporated in vacuo and was shown to be a mixture of two components by TLC. Purification by column chromatography on silica-gel gave a less polar fraction: methyl(1RS,2SR,3SR)-3-[2-(but-1-yl)-4-methoxyphenyl)-1-(3,4-methylenedioxyphenyl)-5-(prop-1-yloxy)indane-2-carboxylate (0.038 g) which was obtained as a colorless oil. The title compound was the more polar component (0.08 g) which while contaminated with tin residues (1H-NMR) was used without further purification.

Workup

  1. temperaturerefluxed for 24 h
  2. filtrationThe product was filtered through celite
  3. washthe celite washed with ethyl acetate
  4. customThe combined filtrate was evaporated in vacuo
  5. additiona mixture of two components by TLC
  6. customPurification by column chromatography on silica-gel
  7. customgave a less polar fraction

Sources & evidence

ORD record
ord-6b491ba4f47c4125a51ce88aeb1c1fa5
Source dataset
uspto-grants-1998_10
Patent number
US05817693

Reaction notes

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