Reaktion #1706

Reaktionsgleichung

Compound 1

7-(Pyridin-4-ylmethoxy)-1,2,3,4-tetrahydronaphthalen-1-one

diisobutylaluminum hydride

→

Compound 2

Ausbeute 78.2%

7-(Pyridin-4-ylmethoxy)-1,2,3,4-tetrahydronaphthalen-1-ol

Ausbeute 78.2%

Lösungsmittel

tetrahydrofuran

toluene

Reaktionsbedingungen

Aufarbeitung

1. 1
   Sonstigethe reaction was quenched with aqueous potassium sodium tartrate
2. 2
   workup.ADDITIONdiluted with ethyl acetate
3. 3
   Sonstigethe layers were separated
4. 4
   Extraktionthe aqueous phase was re-extracted with ethyl acetate (2×)
5. 5
   Waschenwashed with brine
6. 6
   Trocknendried over anhydrous magnesium sulfate
7. 7
   Filtrationfiltered
8. 8
   Einengenconcentrated in vacuo

Vorschrift

To a solution of Compound 1 (16.41 g, 64.9 mmol) in tetrahydrofuran (75 mL) at 0° C. was added dropwise a 1M solution of diisobutylaluminum hydride in toluene (97.3 mL). After 1 hr, the reaction was quenched with aqueous potassium sodium tartrate and diluted with ethyl acetate followed by warming to room temperature. After stirring for an additional hour, the layers were separated and the aqueous phase was re-extracted with ethyl acetate (2×). The extracts were combined, washed with brine, dried over anhydrous magnesium sulfate, filtered and concentrated in vacuo. Chromatography of the residue on silica gel (elution with ethyl acetate) provided 12.96 g of Compound 2 as an oil which crystallized upon standing.

Quelle