Reaktion #669923

Reaktionsgleichung

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

Ausbeute 55.0%

Lösungsmittel

hexane

dichloromethane

Reaktionsbedingungen

Aufarbeitung

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

Vorschrift

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%

Quelle