反応 #1706

反応方程式

Compound 1

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

diisobutylaluminum hydride

→

Compound 2

収率 78.2%

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

収率 78.2%

溶媒

tetrahydrofuran

toluene

反応条件

後処理

1. 1
   その他the reaction was quenched with aqueous potassium sodium tartrate
2. 2
   workup.ADDITIONdiluted with ethyl acetate
3. 3
   その他the layers were separated
4. 4
   抽出the aqueous phase was re-extracted with ethyl acetate (2×)
5. 5
   洗浄washed with brine
6. 6
   乾燥dried over anhydrous magnesium sulfate
7. 7
   ろ過filtered
8. 8
   濃縮concentrated in vacuo

実験手順

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.

出典