7-Bromo-4-methoxy-1H-indene-2,3-dicarboxylic acid, diethyl ester → 4-Methoxy-2,3-dihydro-1H-indene-2,3-dicarboxylic acid, diethyl ester

HRID 5345Notes

Reaction equation

HRID 5345 reaction equation
Br[C:2]1[CH:3]=[CH:4][C:5]([O:21][CH3:22])=[C:6]2[C:10]=1[CH2:9][C:8]([C:11]([O:13][CH2:14][CH3:15])=[O:12])=[C:7]2[C:16]([O:18][CH2:19][CH3:20])=[O:17]>C(O)C.[Pd].[O-]S([O-])(=O)=O.[Ba+2]>[CH3:22][O:21][C:5]1[CH:4]=[CH:3][CH:2]=[C:10]2[C:6]=1[CH:7]([C:16]([O:18][CH2:19][CH3:20])=[O:17])[CH:8]([C:11]([O:13][CH2:14][CH3:15])=[O:12])[CH2:9]2

Participants

4

Reactant 1

HCID 156623417-Bromo-4-methoxy-1H-indene-2,3-dicarboxylic acid, diethyl ester

Product 1

HCID 156623424-Methoxy-2,3-dihydro-1H-indene-2,3-dicarboxylic acid, diethyl esterYield 96.9%

Reagents, catalysts & solvents 2

HCID 16218511Pd barium sulfateCatalystHCID 702EthanolSolvent

Procedure

The diester from Example 2 (19.39 g) was dissolved in 250 ml ethanol. To the solution was added 5.20 g of 10% Pd/BaSO4 and 7.15 g NaOAc.3H2O. The reaction was hydrogenated at 4 atm pressure. The catalyst was filtered and the solvent evaporated. The product was dissolved in ether, washed with 5% NaHCO3, dried (MgSO4), and the solvent was evaporated to yield 14.87 g of the desired product as a colorless oil. NMR (CDCl3) δ1.20 (t, 3H), 1.27 (t, 3H), 3.13 (dd, 1H), 3.48-3.56 (m, 2H), 3.82 (s, 3H), 3.95-4.22 (m, 4H), 4.39 (d, 1H), 6.70 (d, 1H), 6.87 (d, 1H), 7.21 (t, 1H).

Workup

  1. filtrationThe catalyst was filtered
  2. customthe solvent evaporated
  3. dissolutionThe product was dissolved in ether
  4. washwashed with 5% NaHCO3
  5. dry with materialdried (MgSO4)
  6. customthe solvent was evaporated

Sources & evidence

ORD record
ord-09ecf8fbcf7143b4b4b1bb485c9c30d9
Source dataset
uspto-grants-1993_09
Patent number
US05244888

Reaction notes

Loading…