Lithium Chloride → HCID 18427722, compound

HRID 1279320Notes

Reaction equation

HRID 1279320 reaction equation
[Li+].[Cl-].[CH3:3][O:4][C:5]1[CH:10]=[CH:9][C:8]([CH:11]2[C:19]3[C:14](=[CH:15][CH:16]=[C:17]([O:20][CH2:21][CH2:22][CH3:23])[CH:18]=3)[CH:13]([C:24]3[CH:29]=[CH:28][C:27]4[O:30][CH2:31][O:32][C:26]=4[CH:25]=3)[CH:12]2[C:33]([O-:35])=[O:34])=[C:7](OS(C(F)(F)F)(=O)=O)[CH:6]=1.C([Sn]([C:57]1[CH:62]=[CH:61][CH:60]=[CH:59][CH:58]=1)(CCCC)CCCC)CCC>O1CCOCC1.C(OCC)(=O)C.[Pd].C1(P(C2C=CC=CC=2)C2C=CC=CC=2)C=CC=CC=1.C1(P(C2C=CC=CC=2)C2C=CC=CC=2)C=CC=CC=1.C1(P(C2C=CC=CC=2)C2C=CC=CC=2)C=CC=CC=1.C1(P(C2C=CC=CC=2)C2C=CC=CC=2)C=CC=CC=1>[CH3:3][O:4][C:5]1[CH:6]=[CH:7][C:8]([CH:11]2[C:19]3[C:14](=[CH:15][CH:16]=[C:17]([O:20][CH2:21][CH2:22][CH3:23])[CH:18]=3)[CH:13]([C:24]3[CH:29]=[CH:28][C:27]4[O:30][CH2:31][O:32][C:26]=4[CH:25]=3)[CH:12]2[C:33]([OH:35])=[O:34])=[C:9]([C:57]2[CH:58]=[CH:59][CH:60]=[CH:61][CH:62]=2)[CH:10]=1

Participants

7

Reactant 3

HCID 433294Lithium ChlorideHCID 607632TributylphenyltinHCID 21713099HCID 21713099, compound

Product 1

HCID 18427722HCID 18427722, compound

Reagents, catalysts & solvents 3

HCID 11979704Tetrakis(triphenylphosphine)palladiumCatalystHCID 8857Ethyl AcetateSolventHCID 312751,4-DioxaneSolvent2×

Procedure

To a slurry of anhydrous LiCl (46 mg, 1.1 mmol) and tetrakis(triphenylphosphine)-palladium(0) (24 mg, 0.02 mmol) in dry dioxane (3 mL) was added a solution of Methyl (1RS, 2RS, 3RS)-3-(4-Methoxy-2-trifluoromethanesulfonyloxyphenyl)-1-(3,4-methylenedioxyphenyl)-5-(prop-1-yloxy)indane-2-carboxylate (95 mg, 0.16 mmol) and tri(but-1-yl)stannylbenzene (319 mg, 0.87 mmol) in dioxane (1 mL). The mixture was refluxed under Argon for 17 h, cooled to room temperature, diluted with ethyl acetate (5 ml) and the resulting solution washed sequentially with brine and water. The organic layer was dried (MgSO4 anhydrous), filtered through a short pad of silica gel and concentrated in vacuo to yield an oil. The product was purified by flash column chromatography (silica gel, gradient elution from hexanes to 10% ethyl acetate/hexanes) to afford the title compound as a white solid. (92 mg, 86%).

Workup

  1. temperatureThe mixture was refluxed under Argon for 17 h
  2. washthe resulting solution washed sequentially with brine and water
  3. dry with materialThe organic layer was dried (MgSO4 anhydrous)
  4. filtrationfiltered through a short pad of silica gel
  5. concentrationconcentrated in vacuo
  6. customto yield an oil
  7. customThe product was purified by flash column chromatography (silica gel, gradient elution from hexanes to 10% ethyl acetate/hexanes)

Sources & evidence

ORD record
ord-a4f7117bb8c243d7aacc03cb48d4f69c
Source dataset
uspto-grants-2002_09
Patent number
US06448260B2

Reaction notes

Loading…