Hydrogen Peroxide → (RS) 2-hydroxy-4-indanecarbonitrile

Participants

Reaction Conditions

Reaction Steps

42 ml of a 1M solution of boran-tetrahydrofuran complex is cooled to 0° C., 3.7 ml of 2,3-dimethyl-2-butene in 20 ml of tetrahydrofuran is added and agitation is carried out for one hour 15 minutes at 0° C. 1.98 g of product obtained in Stage A in 20 ml of tetrahydrofuran is introduced at 0° C. over 40 minutes, with agitation for 1/4 hour at 0° C., and the temperature is allowed to rise to +14° C. over 3 hours. After cooling to 0° C., 5 ml of water is added drop by drop with agitation for 5 minutes, then 18 ml of 2N sodium hydroxide is introduced at +2° C., and the temperature is allowed to rise to +15° C. 18 ml of hydrogen peroxide at 30% is added slowly and the mixture is left under agitation for 17 hours. The reaction mixture is poured into 100 ml of water and 100 ml of isopropyl ether and decanted; the aqueous phase is extracted with isopropyl ether. The reunited organic phases are washed with water, dried and concentrated to dryness under reduced pressure. The residue is chromatographed on silica in a hexane-ethyl acetate mixture (6-4), and 0.15 g of expected product is obtained, and 1.15 g of impure product is obtained which is chromatographed again on silica in a hexane-ethyl acetate mixture (65-35) so as to obtain 0.74 g of expected product, M.p.=60° C.

Provenance & Evidence