Dimethyl malonate → Dimethyl 5,6-dimethoxyindane-2,2-dicarboxylate

HRID 974027Notes

Reaction equation

HRID 974027 reaction equation
[C:1]([O:8][CH3:9])(=[O:7])[CH2:2][C:3]([O:5][CH3:6])=[O:4].[H-].[Na+].Cl[CH2:13][C:14]1[CH:19]=[C:18]([O:20][CH3:21])[C:17]([O:22][CH3:23])=[CH:16][C:15]=1[CH2:24]Cl>CN(C=O)C>[CH3:23][O:22][C:17]1[CH:16]=[C:15]2[C:14](=[CH:19][C:18]=1[O:20][CH3:21])[CH2:13][C:2]([C:1]([O:8][CH3:9])=[O:7])([C:3]([O:5][CH3:6])=[O:4])[CH2:24]2

Participants

5

Reactant 3

HCID 7943Dimethyl malonateHCID 24758Sodium hydrideHCID 109444001,2-Bis(chloromethyl)-4,5-dimethoxybenzene

Product 1

HCID 19987240Dimethyl 5,6-dimethoxyindane-2,2-dicarboxylateYield 55%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

To a solution of dimethyl malonate (1.7 ml, 14.9 mmol) in DMF (30 ml) at room temperature under nitrogen was added sodium hydride (1.3 g of a 60% dispersion in oil). The mixture was stirred for 20 minutes, and 1,2-bis(chloromethyl)-4,5-dimethoxybenzene (3.5 g, 14.9 mmol) was added. After 16 hours, the mixture was quenched with water and extracted three times with ether. The combined extracts were washed twice with water and dried (McSO4), filtered and evaporated. The residue was dissolved in methylene chloride and filtered through a pad of silica gel. Evaporation gave dimethyl 5,6-dimethoxyindane-2,2-dicarboxylate as a white solid (2.24 g, 55% yield).

Workup

  1. waitAfter 16 hours
  2. customthe mixture was quenched with water
  3. extractionextracted three times with ether
  4. washThe combined extracts were washed twice with water
  5. customdried (McSO4)
  6. filtrationfiltered
  7. customevaporated
  8. dissolutionThe residue was dissolved in methylene chloride
  9. filtrationfiltered through a pad of silica gel
  10. customEvaporation

Sources & evidence

ORD record
ord-a7f8c96ef7004f2bbb3f1d56530124e5
Source dataset
uspto-grants-1991_11
Patent number
US05066658

Reaction notes

Loading…