Reaktion #63997

Reaktionsgleichung

t-butyldimethylsilyl chloride

methyl 3-(R)-methyl-5-hydroxypentanoate

imidazole

dimethylformamide

→

methyl 3-(R)-methyl-5-(t-butyldimethylsilyloxy)pentanoate

Lösungsmittel

water

Reaktionsbedingungen

Aufarbeitung

1. 1
   Extraktionextracted (4×100 ml.) with ether
2. 2
   WaschenThe combined extracts were washed with 10% hydrochloric acid
3. 3
   Trocknena saturated sodium bicarbonate solution, water and a brine solution, and dried over magnesium sulfate
4. 4
   SonstigeRemoval of the solvent
5. 5
   Sonstigegave 121.88 g
6. 6
   workup.DISTILLATIONof crude product which, on distillation
7. 7
   Sonstigegave 107.12 g

Vorschrift

To a solution of 37 g. (0.253 m) of methyl 3-(R)-methyl-5-hydroxypentanoate and 37 g. (0.543 m) of imidazole in 500 ml. of dimethylformamide was added 37 g. (0.249 m) of t-butyldimethylsilyl chloride and the reaction stirred at room temperature for 2 hours. The reaction mixture was poured into water and extracted (4×100 ml.) with ether. The combined extracts were washed with 10% hydrochloric acid, a saturated sodium bicarbonate solution, water and a brine solution, and dried over magnesium sulfate. Removal of the solvent gave 121.88 g. of crude product which, on distillation, gave 107.12 g. of pure product, b.p. 80°-81° C./0.4 torr.

Quelle