Reaktion #82776

Reaktionsgleichung

( 19 )

(E)-Ethyl 3-[cis-(4-tert-Butyldimethylsilyloxycyclohexyl)]-2-methylprop-2-enoate

lithium aluminum hydride

→

alcohol

(E)-3-[cis-(4-tert-Butyldimethylsilyloxycyclohexyl)]-2-methylprop-2-en1-ol

Lösungsmittel

tetrahydrofuran

Reaktionsbedingungen

Aufarbeitung

1. 1
   SonstigeThe reaction was quenched by the slow addition of saturated Rochelle's salt
2. 2
   workup.ADDITIONdiluted with ethyl acetate
3. 3
   SonstigeThe layers were separated
4. 4
   Extraktionthe aqueous layer was extracted with two portions of ethyl acetate
5. 5
   WaschenThe combined organic extracts were washed with water and brine
6. 6
   SonstigeEvaporation and flash chromatography (elution with 1:10 ethyl acetate-hexane)

Vorschrift

To a solution of 300 mg (0.95 mmol) of enoate (19) in 2.0 mL of anhydrous tetrahydrofuran at 25° C. was added 18 mg (0.43 mmol) of lithium aluminum hydride and the resulting mixture was allowed to stir for 30 min. The reaction was quenched by the slow addition of saturated Rochelle's salt and diluted with ethyl acetate. The layers were separated and the aqueous layer was extracted with two portions of ethyl acetate. The combined organic extracts were washed with water and brine and then drive over MgSO4. Evaporation and flash chromatography (elution with 1:10 ethyl acetate-hexane) gave 220 mg of the allyic alcohol (20). 1H NMR (300 MHz, CDCl3) δ 5.34 (d), 3.96 (d), 3.85 (m), 2.26-2.18 (m), 1.64 (d), 1.61-1.34 (m), 1.82 (s), 0.0 (s).

Quelle