Diethyl methylmalonate → 2-Methyl-4-bromo-1-indanone ethylene ketal

HRID 234072Notes

Reaction equation

HRID 234072 reaction equation
[CH3:1][CH:2]1[CH2:10][C:9]2[C:4](=[CH:5][CH:6]=[CH:7][C:8]=2[Br:11])[C:3]1=[O:12].BrC1C=CC=CC=1CBr.C[CH:23](C(OCC)=O)[C:24](OCC)=[O:25].C([O-])([O-])OCC.O.C1(C)C=CC(S(O)(=O)=O)=CC=1.C(=O)([O-])O.[Na+]>C(O)CO>[CH2:24]1[O:25][C:3]2([C:4]3[C:9](=[C:8]([Br:11])[CH:7]=[CH:6][CH:5]=3)[CH2:10][CH:2]2[CH3:1])[O:12][CH2:23]1

Participants

8

Reactant 6

HCID 11857Diethyl methylmalonateHCID 769652-Bromobenzyl bromideHCID 516892Sodium BicarbonateHCID 521998p-Toluenesulfonic acid monohydrateHCID 105371524-Bromo-2-methyl-1-indanoneHCID 53630039Ethylorthoformate

Product 1

HCID 572149092-Methyl-4-bromo-1-indanone ethylene ketal

Reagents, catalysts & solvents 1

HCID 174Ethylene GlycolSolvent

Procedure

To a solution of 4.88 g of 2-methyl-4-bromo-1-indanone derived from 2-bromobenzyl bromide and diethyl methylmalonate in 12 ml of ethylene glycol was added 5.4 ml of ethyl orthoformate. After a catalytic amount of p-toluenesulfonic acid monohydrate was added, the mixture was stirred overnight at room temperature. The reaction mixture was poured into saturated aqueous sodium hydrogen carbonate and extracted with ether. After the organic layer was dried over magnesium sulfate, the solvent was removed by distillation under reduced pressure. The residual concentrate was purified by silica gel column chromatography to give 4.08 g of the title compound.

Workup

  1. extractionextracted with ether
  2. dry with materialAfter the organic layer was dried over magnesium sulfate
  3. customthe solvent was removed by distillation under reduced pressure
  4. concentrationThe residual concentrate
  5. customwas purified by silica gel column chromatography

Sources & evidence

ORD record
ord-dc5a3af1c4ce494d946f803269e9b57f
Source dataset
uspto-grants-1997_01
Patent number
US05594081

Reaction notes

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