HCID 21191709, compound → Methyl 5-methoxy-2,3-dihydro-1H-indene-2-carboxylate

HRID 1909574Notes

Reaction equation

HRID 1909574 reaction equation
[CH3:1][O:2][C:3]1[CH:4]=[C:5]2[C:9](=[CH:10][CH:11]=1)[C:8](=O)[CH:7]([C:13]([O:15][CH3:16])=[O:14])[CH2:6]2>C(O)(=O)C.Cl(O)(=O)(=O)=O>[CH3:1][O:2][C:3]1[CH:4]=[C:5]2[C:9](=[CH:10][CH:11]=1)[CH2:8][CH:7]([C:13]([O:15][CH3:16])=[O:14])[CH2:6]2

Participants

4

Reactant 1

HCID 21191709HCID 21191709, compound

Product 1

HCID 53724337Methyl 5-methoxy-2,3-dihydro-1H-indene-2-carboxylateYield 46%

Reagents, catalysts & solvents 2

HCID 176Acetic AcidSolventHCID 24247Perchloric AcidSolvent

Procedure

A mixture of methyl 5-methoxy-1-oxo-2,3-dihydro-1H-indene-2-carboxylate (5.5 g, 25 mmol) in acetic acid (0.64 M) and perchloric acid (14.9 M) was suspended in a pressure vessel and was shook under a hydrogen atmosphere (30 psi) for 4 hours. The mixture was filtered through a pad of celite and washed with chloroform. The organic phase was washed with water (5×) until the pH was neutral, followed with a wash with brine. The organic layer was dried over sodium sulfate, filtered and concentrated in vacuo. The crude material was purified by silica gel chromatography (0-100% EtOAc in hexanes) to provide methyl 5-methoxy-2,3-dihydro-1h-indene-2-carboxylate (696) (46%).

Workup

  1. customwas suspended in a pressure vessel
  2. filtrationThe mixture was filtered through a pad of celite
  3. washwashed with chloroform
  4. washThe organic phase was washed with water (5×) until the pH
  5. washa wash with brine
  6. dry with materialThe organic layer was dried over sodium sulfate
  7. filtrationfiltered
  8. concentrationconcentrated in vacuo
  9. customThe crude material was purified by silica gel chromatography (0-100% EtOAc in hexanes)

Sources & evidence

ORD record
ord-bcba5693e1194888ba5bdd91a37b090a
Source dataset
uspto-grants-2013_12
Patent number
US08598374B2

Reaction notes

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