Réaction #669923

Équation de réaction

ethylaluminum dichloride

triethylsilane

citric acid

(1RS,4RS)-3-allyl-4-methyl-4-methoxymethoxy-2-cyclopenten-1-yl (t-butyldimethylsilyl) ether

→

(RS)-3-allyl-4-methyl-3-cyclopenten-1-yl (t-butyldimethylsilyl) ether

Rendement 55.0%

Solvants

hexane

dichloromethane

Conditions de réaction

Traitement

1. 1
   workup.ADDITIONwas added under nitrogen
2. 2
   Autreat -78° C.
3. 3
   workup.WAITthe resulting mixture was brought up to -10° C. over 1 hour
4. 4
   AutreThen the reaction liquid
5. 5
   workup.ADDITIONwas poured into ice-
6. 6
   Extractionextracted with diethyl ether
7. 7
   LavageThe ether layer was washed successively with saturated aqueous sodium bicarbonate solution and saturated aqueous sodium chloride solution
8. 8
   Séchagedried over anhydrous magnesium sulfate
9. 9
   workup.DISTILLATIONthe solvent was distilled off under reduced pressure
10. 10
    AutreThe residue thus obtained

Mode opératoire

To a solution mixture of 4.5 g of (1RS,4RS)-3-allyl-4-methyl-4-methoxymethoxy-2-cyclopenten-1-yl (t-butyldimethylsilyl) ether and 50 ml of dichloromethane was added under nitrogen stream 3 ml of triethylsilane by drops at -78° C., and the resulting mixture was stirred for 15 minutes. Thereafter, under the same conditions, 17.5 ml of 0.93 M hexane solution of ethylaluminum dichloride was added by drops and the resulting mixture was brought up to -10° C. over 1 hour. Then the reaction liquid was poured into ice-cooled 5% aqueous solution of citric acid and extracted with diethyl ether. The ether layer was washed successively with saturated aqueous sodium bicarbonate solution and saturated aqueous sodium chloride solution, then dried over anhydrous magnesium sulfate and the solvent was distilled off under reduced pressure. The residue thus obtained was subjected to silica gel column chromatography to obtain 2 g of (RS)-3-allyl-4-methyl-3-cyclopenten-1-yl (t-butyldimethylsilyl) ether. Yield 55%

Source