1,3-Dibromopropane → HCID 58123513, compound

HRID 536680Notes

Reaction equation

HRID 536680 reaction equation
[CH3:1][O:2][C:3]([CH:5]1[C:13]2[C:8](=[CH:9][CH:10]=[CH:11][CH:12]=2)[CH2:7][C:6]1=[O:14])=[O:4].[OH-].[Na+].[Br:17][CH2:18][CH2:19][CH2:20]Br>C(O)C>[CH3:1][O:2][C:3]([C:5]1([CH2:20][CH2:19][CH2:18][Br:17])[C:13]2[C:8](=[CH:9][CH:10]=[CH:11][CH:12]=2)[CH2:7][C:6]1=[O:14])=[O:4]

Participants

5

Reactant 3

HCID 80011,3-DibromopropaneHCID 14798Sodium HydroxideHCID 10888732Methyl 2-oxo-1-indanecarboxylate

Product 1

HCID 58123513HCID 58123513, compound

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent2×

Conditions

Temperature
40 °C

Procedure

A solution of 2-oxo-indan-1-carboxylic acid methyl ester (3.8 g) and NaOH (1 M in water, 20 mL) in ethanol (30 mL) is added dropwise to a solution of 1,3-dibromopropane (10 mL) in ethanol (20 mL) at room temperature. The solution is warmed to 40° C. and stirred at this temperature for 2 d. Then, the solution is concentrated under reduced pressure and ethyl acetate is added to the residue. The resulting mixture is washed with water and brine and dried (MgSO4). After removing the solvent, the residue is purified by chromatography on silica gel (cyclohexane/ethyl acetate 20:1->9:1) to give the title compound as an oil.

Workup

  1. concentrationThen, the solution is concentrated under reduced pressure and ethyl acetate
  2. additionis added to the residue
  3. washThe resulting mixture is washed with water and brine
  4. dry with materialdried (MgSO4)
  5. customAfter removing the solvent
  6. customthe residue is purified by chromatography on silica gel (cyclohexane/ethyl acetate 20:1->9:1)

Sources & evidence

ORD record
ord-284a8432efe043d2a89bb5ad579a3d20
Source dataset
uspto-grants-2014_10
Patent number
US08859580B2

Reaction notes

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