Ethyl bromoacetate → HCID 86623626, compound

HRID 1821027Notes

Reaction equation

HRID 1821027 reaction equation
[CH3:1][O:2][C:3]1[CH:4]=[C:5]2[C:9](=[CH:10][C:11]=1[CH3:12])[C:8](=O)[CH2:7][CH2:6]2.Br[CH2:15][C:16]([O:18][CH2:19][CH3:20])=[O:17]>C1COCC1.[Zn]>[CH3:1][O:2][C:3]1[CH:4]=[C:5]2[C:9](=[CH:10][C:11]=1[CH3:12])[C:8](=[CH:15][C:16]([O:18][CH2:19][CH3:20])=[O:17])[CH2:7][CH2:6]2

Participants

5

Reactant 2

HCID 7748Ethyl bromoacetateHCID 14193755HCID 14193755, compound

Product 1

HCID 86623626HCID 86623626, compoundYield 55.4%

Reagents, catalysts & solvents 2

HCID 23994ZincCatalystHCID 8028TetrahydrofuranSolvent2×

Procedure

To a mixture of activated Zn dust (1.46 g, 22.3 mmol) in THF (10 mL), a solution of 5-methoxy-6-methylindanone (2.62 g, 14.8 mmol, from Step B) from and ethyl bromoacetate (2.14 mL, 19.3 mmol) in THF (15 mL) were added dropwise via cannula. The reaction was heated to reflux for 45 min and cooled to ambient temperature. The reaction was quenched into 2 N HCl and extracted with EtOAc. The organic layer was washed with H2O, brine, dried over MgSO4, and filtered. Solvents were removed in vacuo, and the residue was purified by flash chromatography (5% EtOAc/hexanes) on SiO2 to afford 2.64 g that was recrystallized from hexanes to afford 2.02 g of the title compound as a white solid: 1H NMR (500 MHz, CDCl3) δ 1.35 (t, 3H, J=7.2 Hz), 2.24 (s, 3H), 3.04-3.06 (m, 2H), 3.29-3.31 (m, 2H), 3.88 (s, 3H), 4.23, (q, 2H, J=7.1 Hz), 6.16 (t, 1H, J=2.4 Hz), 6.79 (d, 1H, J=8.8 Hz), 7.38 (d, 1H, J=8.5 Hz).

Workup

  1. temperatureThe reaction was heated
  2. temperatureto reflux for 45 min
  3. customThe reaction was quenched into 2 N HCl
  4. extractionextracted with EtOAc
  5. washThe organic layer was washed with H2O, brine
  6. dry with materialdried over MgSO4
  7. filtrationfiltered
  8. customSolvents were removed in vacuo
  9. customthe residue was purified by flash chromatography (5% EtOAc/hexanes) on SiO2
  10. customto afford 2.64 g that
  11. customwas recrystallized from hexanes

Sources & evidence

ORD record
ord-8307df9d9fbd4a4a88ad05bcb257bd3b
Source dataset
uspto-grants-2009_10
Patent number
US07605171B2

Reaction notes

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