Methyl bromoacetate → HCID 86623633, Verbindung

HRID 1821053Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 1821053
[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

Komponenten

5

Edukt 2

HCID 60984Methyl bromoacetateHCID 787875-Methoxyindan-1-one

Produkt 1

HCID 86623633HCID 86623633, VerbindungAusbeute 72,9 %

Reagenzien, Katalysatoren, Lösungsmittel 2

HCID 23994ZincKatalysatorHCID 8028TetrahydrofuranLösungsmittel2×

Versuchsvorschrift

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).

Aufarbeitung

  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

Quellen und Nachweise

ORD-Eintrag
ord-f27dbbe42c1d4f4da43803b752060909
Quelldatensatz
uspto-grants-2009_10
Patentnummer
US07605171B2

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