Lithium Chloride → Methyl 1,1-dimethyl-3-phenyl-1H-indene-5-carboxylate

HRID 265440Notes

Reaction equation

HRID 265440 reaction equation
[CH3:1][C:2]1([CH3:23])[C:10]2[C:5](=[CH:6][C:7]([C:11]([O:13][CH3:14])=[O:12])=[CH:8][CH:9]=2)[C:4](OS(C(F)(F)F)(=O)=O)=[CH:3]1.[Cl-].[Li+].[C:26]1([Sn](CCCC)(CCCC)CCCC)[CH:31]=[CH:30][CH:29]=[CH:28][CH:27]=1>O.C1C=CC(/C=C/C(/C=C/C2C=CC=CC=2)=O)=CC=1.C1C=CC(/C=C/C(/C=C/C2C=CC=CC=2)=O)=CC=1.C1C=CC(/C=C/C(/C=C/C2C=CC=CC=2)=O)=CC=1.[Pd].[Pd].C1([As](C2C=CC=CC=2)C2C=CC=CC=2)C=CC=CC=1>[CH3:1][C:2]1([CH3:23])[C:10]2[C:5](=[CH:6][C:7]([C:11]([O:13][CH3:14])=[O:12])=[CH:8][CH:9]=2)[C:4]([C:26]2[CH:31]=[CH:30][CH:29]=[CH:28][CH:27]=2)=[CH:3]1

Participants

7

Reactant 3

HCID 433294Lithium ChlorideHCID 607632TributylphenyltinHCID 19034466Methyl 1,1-dimethyl-3-(trifluoromethanesulfonyloxy)-1H-indene-5-carboxylate

Product 1

HCID 19034436Methyl 1,1-dimethyl-3-phenyl-1H-indene-5-carboxylateYield 83.1%

Reagents, catalysts & solvents 3

HCID 11773TriphenylarsineCatalystHCID 9811564Bis(dibenzylideneacetone)palladiumCatalystHCID 962WaterSolvent

Procedure

Methyl 1,1-dimethyl-3-(trifluoromethanesulfonyloxy)-1H-indene-5-carboxylate (580 mg, 1.86 mmol), tris(dibenzylideneacetone)dipalladium (0) (Pd2 dba3, 17 mg, 0.02 mmol), triphenylarsine (46 mg, 0.15 mmol), lithium chloride (240 mg, 5.59 mmol) and phenyltributyltin (680 mg, 1.86 mmol) in 5 mL of 2-methyl pyrrolidinone were stirred at 55° C. for 1.5 days. The mixture was diluted with water (30 mL), and extracted with ethyl ether (30 mL×3). The combined extracts were dried over magnesium sulfate and evaporated. The residue was purified by flash chromatography (EtOAc:hexane=1:20 to 1:5) to give 0.43 g (83% yield) of the title compound as a white solid; 1H-NMR (CDCl3) δ 1.41 (s, 6H), 3.91 (s, 3H), 6.48 (s, 1H), 7.39-7.62 (m, 6H), 7.99 (d, J=6.8 Hz, 1H), 8.14 (s, 1H); MS m/e 279 (MH+).

Workup

  1. extractionextracted with ethyl ether (30 mL×3)
  2. dry with materialThe combined extracts were dried over magnesium sulfate
  3. customevaporated
  4. customThe residue was purified by flash chromatography (EtOAc:hexane=1:20 to 1:5)

Sources & evidence

ORD record
ord-27b6995ad0f54a5f96f6bad701cc368f
Source dataset
uspto-grants-1997_07
Patent number
US05648385

Reaction notes

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