2-Butyl-5-methoxy-2-(3-oxo-pentyl)-1-indanone → 9a-butyl-7-methoxy-4-methyl-1,2,9,9a-tetrahydro-3H-fluoren-3-one

HRID 7825

Reaktionsgleichung

Reaktionsgleichung von HRID 7825
[CH2:1]([C:5]1([CH2:17][CH2:18][C:19](=[O:22])[CH2:20][CH3:21])[CH2:13][C:12]2[C:7](=[CH:8][CH:9]=[C:10]([O:14][CH3:15])[CH:11]=2)[C:6]1=O)[CH2:2][CH2:3][CH3:4]>C(O)(=O)C.Cl>[CH2:1]([C:5]12[CH2:17][CH2:18][C:19](=[O:22])[C:20]([CH3:21])=[C:6]1[C:7]1[C:12](=[CH:11][C:10]([O:14][CH3:15])=[CH:9][CH:8]=1)[CH2:13]2)[CH2:2][CH2:3][CH3:4]

Komponenten

4

Edukt 1

HCID 219909272-Butyl-5-methoxy-2-(3-oxo-pentyl)-1-indanone

Produkt 1

HCID 120457759a-butyl-7-methoxy-4-methyl-1,2,9,9a-tetrahydro-3H-fluoren-3-oneAusbeute 95,4 %

Reagenzien, Katalysatoren, Lösungsmittel 2

HCID 176Acetic AcidLösungsmittelHCID 313Hydrochloric AcidLösungsmittel

Reaktionsbedingungen

Temperatur
100 °C

Versuchsvorschrift

A solution of 2-butyl-5-methoxy-2-(3-oxo-pentyl)-1-indanone (84 mg, 0.28 mmol) in acetic acid (0.5 mL) and 6N HCl (0.5 mL) was stirred and heated in an oil bath at 100° C. for 21 hours. After cooling to room temperature, the reaction mixture was partitioned between EtOAc (20 mL) and water (20 mL). The organic phase was washed with water (10 mL), 5% NaHCO3 (20 mL), and brine (10 mL), dried over MgSO4, filtered, and evaporated under vacuum to afford 9a-butyl-7-methoxy-4-methyl-1,2,9,9a-tetrahydro-3H-fluoren-3-one (76 mg) as a gum.

Aufarbeitung

  1. temperatureAfter cooling to room temperature
  2. customthe reaction mixture was partitioned between EtOAc (20 mL) and water (20 mL)
  3. washThe organic phase was washed with water (10 mL), 5% NaHCO3 (20 mL), and brine (10 mL)
  4. dry with materialdried over MgSO4
  5. filtrationfiltered
  6. customevaporated under vacuum

Quellen und Nachweise

ORD-Eintrag
ord-13b6e50ba0aa46dbbb22df4807534675
Quelldatensatz
uspto-grants-2006_08
Patentnummer
US07087599B2

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