Aluminium lithium hydride → (4-Benzyloxy-6-fluoro-3-methyl-naphthalen-2-yl)-methanol

HRID 1261428

Reaktionsgleichung

Reaktionsgleichung von HRID 1261428
[H-].[H-].[H-].[H-].[Li+].[Al+3].C[O:8][C:9]([C:11]1[C:20]([CH3:21])=[C:19]([O:22][CH2:23][C:24]2[CH:29]=[CH:28][CH:27]=[CH:26][CH:25]=2)[C:18]2[C:13](=[CH:14][CH:15]=[C:16]([F:30])[CH:17]=2)[CH:12]=1)=O>C1COCC1>[CH2:23]([O:22][C:19]1[C:18]2[C:13](=[CH:14][CH:15]=[C:16]([F:30])[CH:17]=2)[CH:12]=[C:11]([CH2:9][OH:8])[C:20]=1[CH3:21])[C:24]1[CH:25]=[CH:26][CH:27]=[CH:28][CH:29]=1

Komponenten

4

Edukt 2

HCID 21226445Aluminium lithium hydrideHCID 593266024-Benzyloxy-6-fluoro-3-methyl-naphthalene-2-carboxylic acid methyl ester

Produkt 1

HCID 59326595(4-Benzyloxy-6-fluoro-3-methyl-naphthalen-2-yl)-methanolAusbeute 92,5 %

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 8028TetrahydrofuranLösungsmittel2×

Versuchsvorschrift

To a suspension of LiAlH4 (8.8 g, 235 mmol) in dry THF (120 mL) was added a solution of 4-benzyloxy-6-fluoro-3-methyl-naphthalene-2-carboxylic acid methyl ester (25.4 g, 78.4 mmol) in THF (180 mL) dropwise at 0° C. under nitrogen. The reaction mixture was stirred at room temperature for 3 hours. After this time, the reaction mixture was cooled to 0° C. and quenched carefully via addition of cold water (10 mL) followed by 15% NaOH solution (10 mL) and additional water. The resulting solution was stirred for one hour, then filtered through a sintered glass funnel. The filter pad was washed with THF (50 mL). The combined filtrates were dried over Na2SO4, filtered, and concentrated to afford (4-benzyloxy-6-fluoro-3-methyl-naphthalen-2-yl)-methanol (21.5 g, 92%, crude) as a white solid. The crude product was used in the next step without further purification. MS cald. for C19H16FO2 [(M−H)+]: 295, obsd. 294.9.

Aufarbeitung

  1. temperatureAfter this time, the reaction mixture was cooled to 0° C.
  2. customquenched carefully via addition of cold water (10 mL)
  3. stirringThe resulting solution was stirred for one hour
  4. filtrationfiltered through a sintered glass funnel
  5. washThe filter pad was washed with THF (50 mL)
  6. dry with materialThe combined filtrates were dried over Na2SO4
  7. filtrationfiltered
  8. concentrationconcentrated

Quellen und Nachweise

ORD-Eintrag
ord-4f762ab74596401895b50ffe650c4de8
Quelldatensatz
uspto-grants-2013_06
Patentnummer
US08470884B2

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