Trimethylsilyldiazomethane → Methyl 3-oxo-2,3-dihydro-1H-indene-5-carboxylate

HRID 2402380Notes

Reaction equation

HRID 2402380 reaction equation
[O:1]=[C:2]1[C:10]2[C:5](=[CH:6][CH:7]=[C:8]([C:11]([OH:13])=[O:12])[CH:9]=2)[CH2:4][CH2:3]1.[Si](C=[N+]=[N-])(C)(C)[CH3:15]>C(Cl)Cl.CO>[O:1]=[C:2]1[C:10]2[C:5](=[CH:6][CH:7]=[C:8]([C:11]([O:13][CH3:15])=[O:12])[CH:9]=2)[CH2:4][CH2:3]1

Participants

5

Reactant 2

HCID 167693TrimethylsilyldiazomethaneHCID 123412861-Indanone-6-carboxylic acid

Product 1

HCID 10081226Methyl 3-oxo-2,3-dihydro-1H-indene-5-carboxylateYield 61.9%

Reagents, catalysts & solvents 2

HCID 887MethanolSolventHCID 6344DichloromethaneSolvent

Procedure

To a solution of 3-oxo-2,3-dihydro-1H-indene-5-carboxylic acid (3 g, 17 mmol) in DCM (50 mL) and MeOH (10 mL) was added TMSCHN2 (17 mL, 34 mmol) dropwise and the mixture was stirred at rt for 1 h. The mixture was concentrated under reduced pressure and the residue was purified by silica gel chromatography using a gradient solvent system of 10:1 to 3:1 petroleum ether/EtOAc to give methyl 3-oxo-2,3-dihydro-1H-indene-5-carboxylate (2.0 g, 61%). MS ESI calcd for C11H10O3 [M+H]+ 191, found 191.

Workup

  1. concentrationThe mixture was concentrated under reduced pressure
  2. customthe residue was purified by silica gel chromatography

Sources & evidence

ORD record
ord-0ac58b98e1db464198c0ce4d5a239182
Source dataset
uspto-grants-2014_08
Patent number
US08796310B2

Reaction notes

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