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

HRID 53280

Reaction equation

HRID 53280 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) δ1.41 (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-99ab55077d4f4d628237162ea7b5467e
Source dataset
uspto-grants-1997_04
Patent number
US05618839

Linked notes

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