Hydrochloric Acid → Methyl 2-(6-methoxy-1H-inden-3-yl)butanoate

HRID 46016

Reaktionsgleichung

Reaktionsgleichung von HRID 46016
[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[CH:14]([CH2:19][CH3:20])[C:15]([O:17][CH3:18])=[O:16].Cl>C1COCC1.[Zn]>[CH3:1][O:2][C:3]1[CH:4]=[C:5]2[C:9]([C:8]([CH:14]([CH2:19][CH3:20])[C:15]([O:17][CH3:18])=[O:16])=[CH:7][CH2:6]2)=[CH:10][CH:11]=1

Komponenten

6

Edukt 3

HCID 313Hydrochloric Acid2×HCID 787875-Methoxyindan-1-oneHCID 95577Butanoic acid, 2-bromo-, methyl ester

Produkt 1

HCID 11402344Methyl 2-(6-methoxy-1H-inden-3-yl)butanoateAusbeute 104,4 %

Reagenzien, Katalysatoren, Lösungsmittel 2

HCID 23994ZincKatalysatorHCID 8028TetrahydrofuranLösungsmittel2×

Reaktionsbedingungen

Temperatur
60 °C

Versuchsvorschrift

An oven dried 5-L four-necked round-bottomed flask was fitted with a thermometer, a condenser, an addition funnel, and a mechanical stirrer. Under Ar protection, a suspension of 5-methoxy-1-indanone (80.0 g, 494 mmol), Zn powder (Lancaster, 56.2 g, 865 mmol) in 2 L anhydrous THF was stirred at 60° C. (internal temperature), while a solution of methyl bromobutyrate (134.1 g, 741 mmol) in 400 mL anhydrous THF was added slowly through an addition funnel. After completion of the addition, the reaction mixture was stirred at 60° C. (internal temperature) for 1 hour. The reaction was followed by TLC analysis of aliquots following 1N aqueous HCl work-up. After the reaction was completed, it was cooled in an ice-water bath followed by slow addition of 3 L of 1N HCl solution. The pot temperature was kept below 20° C. The mixture was then extracted with 1 L EtOAc. The organic layer was washed with water until pH 6.0-7.0, then saturated NaCl solution, and dried over Na2SO4. The product (127 g, >99%), a yellow oil, was obtained after solvent removal and drying under vacuum. 1H NMR (DMSO-d6) δ 7.28 (d, 1H), 7.05 (d, 1H), 6.82 (dd, 1H), 6.22 (s, 1H), 3.72 (s, 3H), 3.60 (m, 1H), 3.58 (s, 3H), 3.28 (s, 2H), 1.95 (m, 1H), 1.80 (m, 1H), 0.88 (t, 3H).

Aufarbeitung

  1. dry with materialAn oven dried 5-L four-necked round-bottomed flask
  2. customwas fitted with a thermometer, a condenser, an addition funnel, and a mechanical stirrer
  3. additionAfter completion of the addition
  4. stirringthe reaction mixture was stirred at 60° C. (internal temperature) for 1 hour
  5. temperatureit was cooled in an ice-water bath
  6. customwas kept below 20° C
  7. extractionThe mixture was then extracted with 1 L EtOAc
  8. washThe organic layer was washed with water until pH 6.0-7.0
  9. dry with materialsaturated NaCl solution, and dried over Na2SO4

Quellen und Nachweise

ORD-Eintrag
ord-75d4465f86f5474e94ad47e3d1da022a
Quelldatensatz
uspto-grants-2013_09
Patentnummer
US08541618B2

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