반응 #1706

반응 방정식

Compound 1

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

diisobutylaluminum hydride

→

Compound 2

수율 78.2%

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

수율 78.2%

용매

tetrahydrofuran

toluene

반응 조건

후처리

1. 1
   기타the reaction was quenched with aqueous potassium sodium tartrate
2. 2
   workup.ADDITIONdiluted with ethyl acetate
3. 3
   기타the layers were separated
4. 4
   추출the aqueous phase was re-extracted with ethyl acetate (2×)
5. 5
   세척washed with brine
6. 6
   건조dried over anhydrous magnesium sulfate
7. 7
   여과filtered
8. 8
   농축concentrated in vacuo

실험 절차

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.

출처