Methyl bromoacetate → HCID 86623633, compound

HRID 1821053Notes

Reaction equation

HRID 1821053 reaction equation
[CH3:1][O:2][C:3]1[CH:4]=[C:5]2[C:9](=[CH:10][CH:11]=1)[C:8](=O)[CH2:7][CH2:6]2.Br[CH2:14][C:15]([O:17][CH3:18])=[O:16]>C1COCC1.[Zn]>[CH3:1][O:2][C:3]1[CH:4]=[C:5]2[C:9](=[CH:10][CH:11]=1)/[C:8](=[CH:14]/[C:15]([O:17][CH3:18])=[O:16])/[CH2:7][CH2:6]2

Participants

5

Reactant 2

HCID 60984Methyl bromoacetateHCID 787875-Methoxyindan-1-one

Product 1

HCID 86623633HCID 86623633, compoundYield 72.9%

Reagents, catalysts & solvents 2

HCID 23994ZincCatalystHCID 8028TetrahydrofuranSolvent2×

Procedure

A solution of 5-methoxy-1-indanone (2.50 g, 15.4 mmol) and methyl bromoacetate (1.84 mL, 20.0 mmol) in THF (15 mL) was added dropwise to a mixture of activated zinc dust (1.51 g, 23.1 mmol) in THF (10 mL). During the addition the reaction mixture reached reflux temperature, which was maintained for an additional hour after the addition was completed. After cooling to ambient temperature, the reaction mixture was poured into ice-cold 2.0 N HCl and extracted into EtOAc. The organic layer was washed with H2O, brine, dried over MgSO4, filtered and concentrated in vacuo. Purification by flash chromatography (10% EtOAc/hexanes) on SiO2 afforded 2.45 g of the title compound: 1H NMR (CDCl3) δ 3.04-3.07 (m, 2H), 3.30-3.33 (m, 2H), 3.77 (s, 3H), 3.85 (s, 3H), 6.19 (t, 1H, J=2.5 Hz), 6.83 (dd, 1H, J=2.3, 8.7 Hz), 6.85 (s, 1H), 7.52 (d 1H J=8.5 Hz).

Workup

  1. additionDuring the addition the reaction mixture
  2. temperaturereached reflux temperature, which
  3. temperaturewas maintained for an additional hour
  4. additionafter the addition
  5. extractionextracted into EtOAc
  6. washThe organic layer was washed with H2O, brine
  7. dry with materialdried over MgSO4
  8. filtrationfiltered
  9. concentrationconcentrated in vacuo
  10. customPurification by flash chromatography (10% EtOAc/hexanes) on SiO2

Sources & evidence

ORD record
ord-f27dbbe42c1d4f4da43803b752060909
Source dataset
uspto-grants-2009_10
Patent number
US07605171B2

Reaction notes

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