Ethyl bromoacetate → HCID 89618008, compound

HRID 1502573Notes

Reaction equation

HRID 1502573 reaction equation
[CH3:1][O:2][C:3]([C:5]1[CH:6]=[C:7]2[C:11](=[CH:12][CH:13]=1)[CH2:10][CH:9]([C:14]([O:16][CH2:17][CH3:18])=[O:15])[C:8]2=[O:19])=[O:4].[H-].[Na+].[CH3:22][CH2:23][O:24][C:25]([CH2:27]Br)=[O:26]>CN(C=O)C>[CH3:1][O:2][C:3]([C:5]1[CH:6]=[C:7]2[C:11](=[CH:12][CH:13]=1)[CH2:10][C:9]([CH2:27][C:25]([O:24][CH2:23][CH3:22])=[O:26])([C:14]([O:16][CH2:17][CH3:18])=[O:15])[C:8]2=[O:19])=[O:4]

Participants

5

Reactant 3

HCID 7748Ethyl bromoacetateHCID 24758Sodium hydrideHCID 89618077HCID 89618077, compound

Product 1

HCID 89618008HCID 89618008, compoundYield 80.1%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent2×

Conditions

Temperature
60 °C

Procedure

To a stirred solution of 3-oxo-indan-2,5-dicarboxylic acid 2-ethyl ester-5-methyl ester (Step 1, 500 mg, 1.9 mmol) in dry DMF (0.7 ml) was added sodium hydride (84 mg, 2.0 mmol, 60% in mineral oil) and then heated at 60° C. for 1 h. Then ethyl bromo acetate (350 mg, 2.0 mmol) was dissolved in dry DMF (1.4 ml) and added to the reaction mixture at room temperature and then again heated at 60° C. for 3 h. After completion of the reaction mixture was concentrated and H2O (5 ml) was added. The suspension was extracted with ethyl acetate and combined organic layer was washed with brine, dried and concentrated. The crude was purified by column chromatography using 20% ethyl acetate-hexane to give the desired compound (530 mg). 1H NMR (400 MHz, CDCl3) d 8.42 (1H, s), 8.30 (1H, d), 7.57 (1H, d), 4.37 (4H, m), 3.92 (3H, s), 3.90 (1H, d), 3.28 (2H, m), 2.90 (1H, d), 1.15 (3H, m) ppm.

Workup

  1. additionadded to the reaction mixture at room temperature
  2. temperatureagain heated at 60° C. for 3 h
  3. concentrationAfter completion of the reaction mixture was concentrated
  4. additionH2O (5 ml) was added
  5. extractionThe suspension was extracted with ethyl acetate and combined organic layer
  6. washwas washed with brine
  7. customdried
  8. concentrationconcentrated
  9. customThe crude was purified by column chromatography

Sources & evidence

ORD record
ord-81ae2c7a679d4065bb980b0546914204
Source dataset
uspto-grants-2015_12
Patent number
US09210929B2

Reaction notes

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