Lithium Chloride → HCID 86752132, compound

HRID 2288165Notes

Reaction equation

HRID 2288165 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-2f7d13ea5b804e01ba034d169fac62f4
Source dataset
uspto-grants-2000_07
Patent number
US06087389

Reaction notes

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