Acetone → (3E,5E)-5-Fluoro-6-(3-methoxymethoxy-5,5,8,8-tetramethyl-5,6,7,8-tetrahydro-naphthalen-2-yl)-octa-3,5-dien-2-one

HRID 1883279Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 1883279
[F:1]/[C:2](=[C:5](/[C:8]1[C:17]([O:18][CH2:19][O:20][CH3:21])=[CH:16][C:15]2[C:14]([CH3:23])([CH3:22])[CH2:13][CH2:12][C:11]([CH3:25])([CH3:24])[C:10]=2[CH:9]=1)\[CH2:6][CH3:7])/[CH:3]=O.[OH-].[Na+].[CH3:28][C:29]([CH3:31])=[O:30]>>[F:1]/[C:2](=[C:5](/[C:8]1[C:17]([O:18][CH2:19][O:20][CH3:21])=[CH:16][C:15]2[C:14]([CH3:22])([CH3:23])[CH2:13][CH2:12][C:11]([CH3:24])([CH3:25])[C:10]=2[CH:9]=1)\[CH2:6][CH3:7])/[CH:3]=[CH:28]/[C:29](=[O:30])[CH3:31]

Komponenten

4

Edukt 3

HCID 180AcetoneHCID 14798Sodium HydroxideHCID 60098606(E)-2-Fluoro-3-(3-methoxymethoxy-5,5,8,8-tetramethyl-5,6,7,8-tetrahydro-naphthalen-2-yl)-pent-2-enal2×

Produkt 1

HCID 12146420(3E,5E)-5-Fluoro-6-(3-methoxymethoxy-5,5,8,8-tetramethyl-5,6,7,8-tetrahydro-naphthalen-2-yl)-octa-3,5-dien-2-oneAusbeute 95 %

Versuchsvorschrift

To a solution of (E)-2-fluoro-3-(3-methoxymethoxy-5,5,8,8-tetramethyl-5,6,7,8-tetrahydro-naphthalen-2-yl)-pent-2-enal (Intermediate 17, 880 mg, 2.5 mmol) in acetone (10 mL) was added 1M NaOH (7.5 mL) at 0° C. The mixture was stirred for 5 h, quenched with 2M H2SO4 (10 mL), and was stirred for 30 min. The mixture was then extracted with EtOAc (×3). The combined organic layer was washed successively with brine, NaHCO3, was dried over MgSO4 and concentrated in vacuo. The residue was purified by flash column chromatography on silica gel (5% EtOAc-hexane) to give the title compound as a yellow solid (930 mg, 95%).

Aufarbeitung

  1. customquenched with 2M H2SO4 (10 mL)
  2. stirringwas stirred for 30 min
  3. extractionThe mixture was then extracted with EtOAc (×3)
  4. washThe combined organic layer was washed successively with brine, NaHCO3
  5. dry with materialwas dried over MgSO4
  6. concentrationconcentrated in vacuo
  7. customThe residue was purified by flash column chromatography on silica gel (5% EtOAc-hexane)

Quellen und Nachweise

ORD-Eintrag
ord-34c72f44d0ec437887d43242839f8029
Quelldatensatz
uspto-grants-2004_07
Patentnummer
US06759547B1

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