Реакция #1706

Уравнение реакции

Compound 1

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

diisobutylaluminum hydride

→

Compound 2

Выход 78.2%

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

Выход 78.2%

Растворители

tetrahydrofuran

toluene

Условия реакции

Обработка

1. 1
   Другоеthe reaction was quenched with aqueous potassium sodium tartrate
2. 2
   workup.ADDITIONdiluted with ethyl acetate
3. 3
   Другоеthe layers were separated
4. 4
   Экстракцияthe aqueous phase was re-extracted with ethyl acetate (2×)
5. 5
   Промывкаwashed with brine
6. 6
   Сушкаdried over anhydrous magnesium sulfate
7. 7
   Фильтрацияfiltered
8. 8
   Концентрированиеconcentrated in vacuo

Методика

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.

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