Methanol → (E)-(3-(5-(1,1,1,3,3,3-hexafluoro-2-(methoxymethoxy)propan-2-yl)-3-(prop-1-enyl)pyridin-2-yloxy)phenyl)methanol

HRID 1690149Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 1690149
[F:1][C:2]([F:33])([F:32])[C:3]([C:12]1[CH:13]=[C:14](/[CH:29]=[CH:30]/[CH3:31])[C:15]([O:18][C:19]2[CH:20]=[C:21]([CH:26]=[CH:27][CH:28]=2)[C:22](OC)=[O:23])=[N:16][CH:17]=1)([O:8][CH2:9][O:10][CH3:11])[C:4]([F:7])([F:6])[F:5].[H-].[Al+3].[Li+].[H-].[H-].[H-].CO.O>O1CCCC1>[F:33][C:2]([F:1])([F:32])[C:3]([C:12]1[CH:13]=[C:14](/[CH:29]=[CH:30]/[CH3:31])[C:15]([O:18][C:19]2[CH:20]=[C:21]([CH2:22][OH:23])[CH:26]=[CH:27][CH:28]=2)=[N:16][CH:17]=1)([O:8][CH2:9][O:10][CH3:11])[C:4]([F:7])([F:6])[F:5]

Komponenten

6

Edukt 4

HCID 887MethanolHCID 962WaterHCID 21226445Aluminium lithium hydrideHCID 59201011methyl (E)-3-(5-(1,1,1,3,3,3-hexafluoro-2-(methoxymethoxy)propan-2-yl)-3-(prop-1-enyl)pyridin-2-yloxy)benzoate

Produkt 1

HCID 59201010(E)-(3-(5-(1,1,1,3,3,3-hexafluoro-2-(methoxymethoxy)propan-2-yl)-3-(prop-1-enyl)pyridin-2-yloxy)phenyl)methanolAusbeute 95 %

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 8028TetrahydrofuranLösungsmittel

Versuchsvorschrift

To a solution of methyl (E)-3-(5-(1,1,1,3,3,3-hexafluoro-2-(methoxymethoxy)propan-2-yl)-3-(prop-1-enyl)pyridin-2-yloxy)benzoate (81 mg, 0.168 mmol) in tetrahydrofuran (2 mL), lithium aluminum hydride (9.6 mg, 0.252 mmol) was added under ice-cold conditions, and the resultant mixture was stirred at room temperature for 3 hours. The reaction solution was added with methanol and water, filtered using celite, and extracted with ethyl acetate. The organic layer was washed with brine, dried using anhydrous sodium sulfate, and concentrated in vacuo. The obtained residue was purified using silica-gel column chromatography (ethyl acetate), and the title compound (72 mg, yield 94.9%) was obtained as a yellow oil.

Aufarbeitung

  1. filtrationfiltered
  2. extractionextracted with ethyl acetate
  3. washThe organic layer was washed with brine
  4. customdried
  5. concentrationconcentrated in vacuo
  6. customThe obtained residue was purified

Quellen und Nachweise

ORD-Eintrag
ord-106a19d435ef47c78fe170ac40f7fb78
Quelldatensatz
uspto-grants-2012_04
Patentnummer
US08153634B2

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