تفاعل #1706

معادلة التفاعل

Compound 1

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

diisobutylaluminum hydride

→

Compound 2

المردود 78.2%

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

المردود 78.2%

المذيبات

tetrahydrofuran

toluene

ظروف التفاعل

المعالجة

1. 1
   أخرىthe reaction was quenched with aqueous potassium sodium tartrate
2. 2
   workup.ADDITIONdiluted with ethyl acetate
3. 3
   أخرىthe layers were separated
4. 4
   استخلاصthe aqueous phase was re-extracted with ethyl acetate (2×)
5. 5
   غسيلwashed with brine
6. 6
   تجفيفdried over anhydrous magnesium sulfate
7. 7
   ترشيحfiltered
8. 8
   تركيزconcentrated in vacuo

الإجراء التجريبي

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.

المصدر