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

HRID 70278Notes

Reaction equation

HRID 70278 reaction equation
[CH3:1][C:2]1([C:12]([O:14][CH3:15])=[O:13])[CH2:10][C:9]2[C:4](=[CH:5][CH:6]=[CH:7][CH:8]=2)[C:3]1=O>CC(O)=O.[Pd]>[CH3:1][C:2]1([C:12]([O:14][CH3:15])=[O:13])[CH2:10][C:9]2[C:4](=[CH:5][CH:6]=[CH:7][CH:8]=2)[CH2:3]1

Participants

4

Reactant 1

HCID 12522314Methyl 2-methyl-1-oxo-2,3-dihydro-1H-indene-2-carboxylate

Product 1

HCID 57565328Methyl 2-methyl-2,3-dihydro-1H-indene-2-carboxylate

Reagents, catalysts & solvents 2

HCID 23938PalladiumCatalystHCID 176Acetic AcidSolvent

Procedure

A mixture of the methyl 2-methyl-1-oxo-2,3-dihydro-1H-indene-2-carboxylate (2.04 g, 9.99 mmol) and 10% Pd/C (0.200 g; wet) in HOAc/conc H2SO4 (22/2 mL respectively) was hydrogenated under 50 psi H2 for 4 h using a Parr hydrogenation apparatus. The mixture was filtered through Celite (2×MeOH wash) and the filtrate was partially concentrated in vacuo. The residue was neutralized with satd Na2CO3 and the whole was extracted with EtOAc (2×25 mL). Combined organics were washed with brine, dried over Na2SO4 and concentrated in vacuo affording the title compound. 1H NMR (400 MHz, CDCl3) δ ppm 1.35 (s, 3H), 2.81 (d, J=15.6 Hz, 2 H), 3.47 (d, J=15.6 Hz, 2 H), 3.71 (s, 3H), 7.12-7.23 (m, 4H).

Workup

  1. filtrationThe mixture was filtered through Celite (2×MeOH wash)
  2. concentrationthe filtrate was partially concentrated in vacuo
  3. extractionthe whole was extracted with EtOAc (2×25 mL)
  4. washCombined organics were washed with brine
  5. dry with materialdried over Na2SO4
  6. concentrationconcentrated in vacuo

Sources & evidence

ORD record
ord-fb7e55d6e310483e97c13ea2cd798f41
Source dataset
uspto-grants-2014_09
Patent number
US08822518B2

Reaction notes

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