Acetic Acid → Methyl 5-methoxy-2,3-dihydro-1H-indene-2-carboxylate

HRID 747971Notes

Reaction equation

HRID 747971 reaction equation
[CH3:1][O:2][C:3]([CH:5]1[CH2:13][C:12]2[C:7](=[CH:8][C:9]([O:14][CH3:15])=[CH:10][CH:11]=2)[C:6]1=O)=[O:4].C(O)(=O)C.Cl(O)(=O)(=O)=O>[Pd].C(OCC)(=O)C>[CH3:1][O:2][C:3]([CH:5]1[CH2:6][C:7]2[C:12](=[CH:11][CH:10]=[C:9]([O:14][CH3:15])[CH:8]=2)[CH2:13]1)=[O:4]

Participants

6

Reactant 3

HCID 176Acetic AcidHCID 24247Perchloric AcidHCID 16639026HCID 16639026, compound

Product 1

HCID 53724337Methyl 5-methoxy-2,3-dihydro-1H-indene-2-carboxylateYield 65%

Reagents, catalysts & solvents 2

HCID 23938PalladiumCatalystHCID 8857Ethyl AcetateSolvent

Procedure

Combine in a Parr shaker 6-Methoxy-1-oxo-indan-2-carboxylic acid methyl ester (3.14 g, 14.25 mmol), added acetic acid (150 mL), perchloric acid (0.8 mL) and 5% Pd—C (0.14 mmol). After the reaction has been on the parr shaker under 40 atm of H2 pressure at room temperature for 12 hours, filter the reaction mixture through a pad of Celite using ethyl acetate eluent. Then add the filtrate to a separatory funnel and wash with water then brine, and dry the organic layer over Na2SO4. After concentrating under reduced pressure, flash Chromatograph using 8:1 Hexanes:Ethyl acetate to afford 1.9 g, 9.21 mmol (65% yield) of the title compound as a clear oil: 1H NMR (500 MHz, CDCl3); 3.2-3.4 (5H, m), 3.7 (3H, s), 3.8 (3H, s), 6.7-6.8 (2H, m), 7.1-7.2 (1H, m); TLC 1:1 Hexanes:Ethyl acetate Rf:=0.6.

Workup

  1. filtrationfilter the reaction mixture through a pad of Celite
  2. additionThen add the filtrate to a separatory funnel
  3. washwash with water
  4. dry with materialbrine, and dry the organic layer over Na2SO4
  5. concentrationAfter concentrating under reduced pressure, flash Chromatograph

Sources & evidence

ORD record
ord-eaa6c74e888647fdb5ddf495554ded70
Source dataset
uspto-grants-2008_07
Patent number
US07399774B2

Reaction notes

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